TW503237B - Intermediate in manufacture of heterocyclic compounds having anti-diabetic activity - Google Patents

Abstract

There is provided an important intermediate compound of formula (I) useful in the preparation of a compound of formula (II), having an excellent biological activities. Compound of formula (I); compound of formula (II): wherein: X represents an unsubstituted or substituted indolyl, indolinyl, azaindolyl, azaindolinyl, imidazopyridyl or imidazopyrimidinyl group; Y represents an oxygen or sulfur atom; Y' represents an oxygen atom or a sulfur atom; Q represents a lower alkoxycarbonyl group, a formyl group, a protected formyl group, a carboxyl group or a hydroxy group; R represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a hydroxy group, a nitro group, an aralkyl group or a unsubstituted or substituted amino group; and m is an integer of from 1 to 5.

Description

503237 A7 B7 V. Description of the invention () Background of the invention The present invention relates to a series of intermediates for the production of heterocyclic compounds having hypoglycemic and anti-diabetic activities. It is known that compounds similar to this heterocyclic compound, which contain other carbazidinedione or diazoridinone groups attached to the benzene ring via a methyl or methylene group, have this type of activity. This general type of compound is shown in the European patent. Bulletin No. 008203, 139 (21, 4 4 1605, 208420, 528734, 177353, 30622 8 vo 356 with 14, and W092 / 0/8 50, 92/07839, 91/07107, 92 / Ο25 / 2〇 and 32 / 03425. We have now discovered that certain fixed bicyclic nitrogen-containing ring systems contained in such compounds result in compounds with improved activity. A brief summary of the invention Therefore, one object of the present invention is to provide important intermediates to make a compound. List of novel chemical compounds, which are considered as thiazolium and azole derivatives. Therefore, the present invention provides compounds of formula (I) and their salts:

Q— (CH2) E

Binding

Staff Association of the Central Standards Bureau of the Ministry of Economic Affairs

(I) Where:.. V. 0 Q is a low alkoxycarbonyl group, a methylamino group, a protected methylamidino group, a chloro or hydroxy group Y is 0 or S; Y · is 0 or S; -3 ~ this paper size Applicable to China National Standard (CNS) A4 specification (210x297 mm) 503237 A7 B7 V. Description of the invention () R is hydrogen atom, Ci-4 alkyl group, Ci-4 alkoxy group, halogen atom, hydroxyl group, nitro group, aromatic group Alkyl where Ci-5 alkyl is an aryl group substituted with 6 to 10 ring sulfo atoms, or the formula Rb, where Ra and! ^ Is the same or different and each is a hydrogen atom, Ci-8 alkyl group, aralkyl group wherein Ci-5 alkyl group is an aryl group substituted with 6 to 10 ring atoms, and 6 to 10 ring atoms Aryl, Lu aliphatic carboxylic acid fluorenyl, C2-6 aliphatic carboxylic acid fluorenyl and substituted with an aryl having 6 to 10 ring sulfo atoms, or an aromatic carboxyl group in which the aryl moiety has 6 to 10 ring sulfo atoms, ro is an integer of 1 to 5. This intermediate can be transformed into a compound of formula (II) with biological activity ^ ch2) ^ y

Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs where: X is indino, indolino, azinoline, azindolinyl, oxazopyridyl or oxazolopyrimidyl, which is unsubstituted Or substituted with at least one substituent is selected from the substituents α defined below; R, Υ, Υ 1 and ο are the same as before. -4- This paper size applies to the Chinese National Standard (CNS), Yasugi 1 cell (21〇 × 297 mm) 503237 A7 B7 V. Description of the invention () Each of the substituents "is (^-4 alkyl, C6-! 〇 Aryl, trifluoromethyl, Cl-4 alkylthio, Cl-4 alkoxy, benzyloxy, halogen atom, hydroxyl, acetamino, phenylthio, nitro, aralkyl, or formula- NRaRb, where 11 and 1 ^ are as defined above; the aryl part of the square group and the aralkyl group contained in the substituent or is a macrocyclic aromatic group having 6 to 10 ring sulfo atoms and is unsubstituted or substituted Substitution with at least one substituent is selected from the substituents defined below; each of the substituent points is Ci-4 alkyl, Ci-4 alkoxy, halogen atom, hydroxyl, nitro, phenyl, trifluoromethyl , Or formula-NRaRb, where 1 ^ and 111) are as defined above. Hairpin: > In the compound of the present invention, in the case where X is a group derived from an indine ring, it may be, for example, indino-1-yl, indino-2-yl, indino-3- The base is Indio-4-¾, B is referred to as a 5 ore base, and the heterogeneous reference medium is made up of 6 bases or B is referred to as a 7-base. With respect to X being a group derived from an indolinoline ring, it may be, for example, indinoline-1-yl, indinoline-2-yl, indolinolin-3-yl, indolin-4-yl, ind Idololin-5-yl, indolin-6-yl or indolin-7-yl. In terms of X being a group derived from an acridine ring, it may be, for example, 4-azindino-1 -yl, 4-azindole-2 -yl, 4-azindole-3 -yl, 4- Acridine-4--4-, 4-by-J, IT-dosyl-5-yl, 4-xia-yamidine, hexadecyl-6-yl, 4-ιιγ bsi ¢ ^ -7-yl, 5-acridin- 1-based, 5-acridin-2-yl, 5-acridin-3-yl, 5-? 11, 5 -yl, 5-y, 5 -yl, "5 Cranes", yB 6-yl, 5-azindino-7-yl, 6-azinine-phenyl, 6-azindin-2-yl, 6-azine β- 3-based, 6-acridinyl-4-based, 6-acridinyl-5-based, 6-acridin-5- This paper is sized for China National Standard (CNS) A4 (210 X 297) Li) Please read the note on the back first. Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs. Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs. 503237 A7 B7. D-7-yl, 7-azindol-1-yl, 7-azindol IT-2-2-, 7-fluorene P3I-3-S, 7-1 yah -ΠΓ Β to give a 5-base, 7-11 γ (if -6-base. Derived from X In terms of the radical of the acridineline ring, it may be, for example, 4-azindino-1-yl, 4-azindolin-2-yl, 4-azindolin-3-yl, 4-azindin Indolin-5-yl, 4-azindolin-6-yl, 4-azindolin-7-yl, 5-azolinolin-yl, 5-azindolin-2-yl, 5-azinolinolin-3-yl, 5-azinolinolin-4-yl, 5-azindolin-6-yl, 5-azindolin-7-yl, 6-azindolinyl -1 -yl, 6-azindolin-2-yl, 6-azinyl-B-indol-6-yl, 6-azindolinyldi 4-yl, 6-azindolinyl-5 -yl , 6-azindinoline-7-yl, 7-azindolinyl-? Yl,? -Azindolin-2-yl, 7 · mr p, a 3 -yl, 7-rr p If it is a 4-base, 7-rr p, it is a 5-base or abuindolin-6. Based on X being a radical derived from an oxazolopyridine ring, it may be, for example, Azolo [4,5-b] pyridin-1-yl, oxazo [4,5-b] pyridin-2-yl, oxazo [4,5-b] pyridin-7-yl, oxazolo [4,5-b] pyridin-5-yl, insomnia and [4,5-b] phenotypic-6-yl, insomnia [4,5-c] pyridin-1-yl, oxazo [ 4,5-c] pyridin-2-yl, oxazo [4,5-c ] Pyridin-4-yl, oxazo [4,5-c] pyridin-6-yl, oxazo [4,5-c] pyridin-7-yl, imidazo [5,4-b] pyridine- 3-yl, oxazolo [5,4-b] Sftpyridin-2-yl, oxazolo [5,4-b] pyridin-7-yl, oxazolo [5,4-b] pyridine-5 -Yl, imidazo [5,4-b] pyridin-6-yl, oxazolo [5,4-c] pyridin-3-yl, oxazolo [5,4-c] pyridin-2-yl, Imidazo [5,4-c] pyridin-4-yl, pyrazolo [5,4-c] -6 ~ This paper size applies to China National Standard (CNS) A4 (210X297 mm) (Please read the back first Please pay attention to this page before filling in this page) • Packing _ 503237 A7 B7 V. Description of the invention () Please read the notes on the back of%. Pyridine-6-yl, pyrazolo [5,4-c] pyridine-7-yl, Oxazolo [1,2-a] pyridin-2-yl, oxazolo [i, 2-a] pyridin-3-yl, oxazolo [1,2-a] pyridin-8-yl, oxazolyl And [1,2-a] pyridin-5-yl, oxazo [1,2-a] pyridin-6-yl or oxazo [1,2-a] pyridin-7-yl. With respect to X being a group derived from an imidazopyrimidine ring, it may be, for example, oxazo [4,5-b] pyrimidin-7-yl, oxazo [4,5-b] pyrimidin-8-yl, or Oxazo [4,5-b] pyrimidin-9-yl. Any group represented by the above X may be unsubstituted or may be substituted with at least one of the substituents α as defined above and listed below. In terms of substitution, there is no particular limitation on the number of substituents, except for the number of substitutable positions, or occasionally limited by steric hindrance. However, 1 to 3 値 substituents are generally preferred, and 1 or 2 値 substituents are most preferred. There is no particular restriction on the position of any such substituent. RC, based on the chain group methyl group C, the group «member generation 4β, take 4 groups ^ _ Shen 2 μ, C, ¾ ¾, 罾 from Γ m for g group Θ package T group Jtll ^ ^ 0 two, or fl The base α, * or Jiayizhi is printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs. The base is oxo, its ethoxy, methoxymethoxy alkane, and the base is substituted. Alkyl 4 generation-Take 1 CR bond to the branch or radical and dioxobutyryl isopropyl group, and the alkyl radical is Ding Jia, which is more than the radicals, isopropyl, oxetane tripropadiene Basic substitution or a basic substitution is based on original iodine 0 or fluoro, which is the scent R > original bromochlorine is noodles, and original 0 is bromine. The scale is applicable to the Chinese National Standard (CNS) A4 specification (210 X 297 mm) 503237 A7 B7 V. Description of the invention () In terms of R being an aralkyl group, the alkyl portion of this group has 1 to 5 sulfonium atoms and can be The straight or branched fluorenyl group substituted by an aryl group may itself be one as defined above and listed below. The aralkyl group preferably has 7 to 11 sulfonium atoms in total. Examples of such alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, second butyl, third butyl, pentyl, isopentyl, neopentyl And tertiary amyl, preferably methyl and ethyl. Examples of aryl are those enumerated below with regard to the substituent σ. Specific examples of such aralkyl groups include benzyl, 2-phenethyl (diphenethyl), 1-phenethyl, 3-phenylpropyl, 2-phenylpropyl, 1-phenylpropyl, 4- Phenylbutyl, 1-phenylbutyl, 5-phenylpentyl, 1- # methyl and 2-naphthylmethyl, with phenethyl and benzyl being preferred, and benzyl being most preferred. In addition, R, substituent α or substituent > 3 may be an amine group or a substituted amine group of the formula-NRaRb, which may be the same or different and selected from the following: (Please read the precautions on the back before filling this page) (1) Hydrogen atom; (2) C 1-8 alkyl group which can be a straight or branched chain group such as methyl 9 ethyl $ propyl f isopropyl butyl 9 Isobutyl 9 second butyl 9 third butyl $ pentyl $ 2-pentyl > 3-pentyl f 2-methylbutyl J 3-methylbutyl 1, 1-dimethylpropyl f 1, 2 · dimethylpropyl 9 2, 1-dimethylpropylhexyl 9 2-hexyl t 3-hexyl f methylpentyl 9 3-methylpentyl $ 4-methylpentyl 9 1 , 1-dimethylbutyl t 1, 2-dimethylbutyl t 1, 3-dimethylbutyl 9 2, 2-. Dimethylbutyl f 2, 3-dimethylbutyl% 3,3-'dimethylbutyl f 1,1,2-.rr methylpropyl $ 1,2,2 -'- methylpropyl * heptyl $ 2-heptyl $ 3-.heptyl 9 4-.heptyl $ 3,3-. Methylpentyl »Octyl 9 -8 ~ This paper size is applicable to Chinese National Standard (CNS) A4 (210X297 mm) Printed by the Staff Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 503237 A7 _B7__ V. Description of the invention () 1-A Heptyl, 2-ethylhexyl and 1,1,3,3-tetramethylbutyl, of which Ci-6 alkyl is preferably straight or branched, and C1 is most preferably straight or branched -4 alkyl groups; methyl and ethyl are preferred; (3) aralkyl groups as defined above and listed below with respect to R, and such groups preferably have 7 to 11 sulfonium atoms; (4) C6-10 aryl groups, such as phenyl, p-naphthyl, and 2-naphthyl; (5) aliphatic carboxylic acid fluorenyl groups, which may be straight or branched Ci-u, for example, methylamino, ethylamino, propylamino , Butyl fluorenyl, isobutyl fluorenyl, pentyl fluorenyl, pentyl fluorenyl, hexyl fluorenyl, heptyl, octyl fluorenyl, nonyl fluorenyl, decyl fluorenyl and undecyl fluorenyl; (6) C2-6 aliphatic carboxylic acid fluorenyl And may be substituted by an aryl group as defined above, each of which preferably has a total of 8 to 12 sulfonium atoms; an example of an aliphatic fluorenyl moiety is C2- contained in the aliphatic fluorenyl group represented by the above fluorene 3, Rb 6 醯Groups (preferably ethenyl and propionyl), and examples of the aryl moiety are those included in the above-mentioned aryl groups (preferably phenyl and naphthyl, to be phenyl); more preferred Specific examples of the aromatic-substituted aliphatic fluorenyl group include phenethylfluorenyl, 3-phenylpropylfluorenyl, 4-phenylbutylfluorenyl, 5-phenylpentylfluorenyl, 6-phenylhexylfluorenyl, α-methylphenethylfluorenyl And or, cr-dimethylphenethylfluorenyl, of which phenethylfluorenyl is preferred; (7) sulfo ring aromatic carboxylic acid group, in which aryl is as defined and listed above (preferably phenyl and naphthyl , To be other than phenyl); the preferred group is one having 7 to 11 desulfuric atoms, and examples thereof include benzylfluorenyl, 1-naphthylfluorenyl, and 2- # fluorenyl, with benzylfluorenyl being preferred. -9- This paper size is in accordance with Chinese National Standard (CNS) A4 (210X297 mm) (Please read the precautions on the back before filling out this page)-Binding and printing printed by the Central Consumers Bureau of the Ministry of Economic Affairs Consumer Cooperative 503237 A7 B7 V. Description of the invention () R, Substitute α or other examples of such amine groups represented by the substituents include the following: U) Substituted amine groups in which one of Ra and Rb is a hydrogen atom and the other Ra and Rb are Alkyl groups such as methylamino, ethylamino, propylamino, isopropylamine, butylamine, isobutylamine, second butylamino, third butylamino, pentylamino, 2-pentylamino, 3-pentylamino, 2-methylbutylamino, 3-methylbutylamino, 1,1-dimethylpropylamine, 1,2-dimethylpropylamine, 2,2-dimethylpropylamine Methyl, hexylamino, 2-hexylamino, 3-hexylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutyl Amine, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethylbutylamino, 3,3 -Dimethylbutylamino, 1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino, heptylamine, 2-heptyl Base, 3-heptylamino, 4-heptylamino, 3,3-dimethylpentylamino, octylamino, 1-methylheptylamino, 2-ethylhexylamino and 1,1,3 , 3-tetramethylbutylamino; (2) a substituted amine group, wherein one of RaRb is a hydrogen atom and the other Ra and Rb are aralkyl groups, such as benzylamino, 2-phenylethylamino, 1-Phenethylamino, 3-Phenylamino, 2-Phenylamino, 1-Phenylamino, 4-Phenylamino, 1-Phenylamino, 5-Phenylamino, 1-Naphthylamino and 2-naphthylmethylamino; (3) substituted amines, one of which is a hydrogen atom and the other Ra * Rb is an aryl group, such as aniline, 1-lylamido and 2-naphthylamine; -10- This paper size applies to China's "National Standards (CNS) A4 specifications (210X297 mm) (Please read the precautions on the back before filling out this page)."-Tr 503237 Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 5. Description of the invention () (4) A substituted amine group, one of which is a hydrogen atom and the other 1 ^ and 1 ^ are aliphatic fluorenyl groups, such as methylamino, propylamino, butylamino, Isobutyrimidine, pentamidine, pentamidine, hexamidine, heptylamine, Fluorenylamino, nonamylamino, decylamino and undecylamino; (5) substituted amines, one of which is a hydrogen atom and the other 1 ^ and 1 ^ are aromatic substituted aliphatic fluorenyl groups, Such as acetophenamino, 3-phenylpropanamido, 4-phenbutaminino, 5-phenpentamidine, 6-phenylhexamide, α-methylphenethylamino and cr , cr-dimethylphenethylamino group; (6) substituted amine group, in which Ra and Rb are hydrogen atoms and other Ra and Rb are aromatic fluorenyl groups, such as benzyl fluorenyl, naphthylamino Naphthylamine; (7) substituted amines, where Ra and Rb are both alkyl groups, each of which may be the same or different, such as dimethylamino, diethylamino, N-methyl-N-ethylamine And N-methylpentylamino; (8) substituted amino groups, in which one of 1 ^ and 1 ^ is an alkyl group and the other! And 1 ^ are aralkyl groups, such as N-ethyl-N- Benzylamino, N-tert-butyl-N-benzylamino and N-hexylbenzylamino; (9) substituted amino, wherein one of Ra and Rb is alkyl and the other 1 and 1 are Aryl, such as N-methyl-N-aniline, N-ethyl-N-aniline and N-octyl-N-aniline; (10) substituted amine groups, one of 1 ^ and 1 ^ Is alkyl and others -11- This paper size applies to the Chinese National Standard (CNS) grid (210X297 mm) (please read the precautions on the back before filling out this page) • Install · 1T. «Printed by the Central Consumers Bureau of the Ministry of Economy System 503237 A7 B7 V. Description of the invention ()

RalRb is an aliphatic fluorenyl group, such as N-propylacetamido, N-pentyl-butyric acid amine, and ethyl-butanal amine, (11) substituted amines, one of which is an alkane Ki and other Ra sum! ^ Aromatic-substituted carboxylic acid aliphatic fluorenyl groups, such as N-ethyl-N-phenylethylfluorenylamino, isopropyl-phenyl (2-phenylpropanyl) amino, and N-methyl-N- (6-phenylhexyl) amino; (12) substituted amine, wherein one of Ra * Rb is alkyl and the other 1 ^ and 1 ^ are aromatic fluorenyl groups, such as N-methylbenzylfluorenylamino (B) a second butyl benzamidine group and an N-heptyl benzamidine group; (13) a substituted amine group, wherein 1 ^ and ^ are both aralkyl groups, each of which may be the same or different, such as dibenzyl Amine group, N-benzyl-N- (3-phenylpropyl) amino group and N-benzyl-N- (2-naphthylmethyl) amine group; (14) Substituted amino groups, of which Ra and Rb One is aralkyl and the other 1 ^ and 1 ^ are aryl groups, such as N-benzylaniline and N- (3-phenylpropyl) -N-aniline; (15) substituted amino groups, of which One is an aralkyl group and the other Ra and Rb are aliphatic groups, such as N-benzyl-N-acetamidino, N-benzyl-propanamidino and N-benzylpentaminino; (16 ) Substituted amine groups, where one of 1 ^ and 1 ^ is aromatic and the other 1 ^ and 1 ^ are aromatic-substituted aliphatic carboxylic acid fluorenyl groups, such as N-benzyl-N-phenylethylfluorenylamino And N-benzyl-N- (4-phenylbutamidino) amine (17) Substituted amine group, one of which is aralkyl group and others -12- This paper size applies to Chinese National Standard (CNS) A4 specification (210X297 mm) (Please read the precautions on the back before filling in this Page)

, 1T 503237

A B7 indicates that penta-Hexylamine, benzyl, N-benzyl-N, and the like; aldolamine is benzyl- b NRI α) f group a R ethyl phenyl aromatic is 1 b R and a The base amine in R is replaced by the base amine, which is not the same or in the same phase, and the base is phenylphenylnaphthylamine phenyl hydrazone, and the acid carboxamide family is replaced by b R 19 and Other radicals are b R with 1 and radicals such as and amines 0 prop-N-yl phenyl, and radicals T amine aromatics are taken as b \ 7 R 20 and radicals IN and radicals 0 radicals Rbil and acids T a carboxyl, diphenyl, lipid, f I its amine 醯 ethyl _, T yl amine benzene II N hexyl fluorinated amine aryl is acetophenone and its N- and-(Please read the back first For the matters needing attention, please fill in this page again.) In the base group, _, the acid carboxyamine aromatized aromatic group is taken as b \ 1 / R 21 and Hezhi group b benzene other and the base aromatic group is benzyl group 醯 benzyl group 醯The amine # is replaced by 2 and is substituted by N \ — / * 2 groups (2 phenylamino 0 acid carboxylic aliphatic amines are the basic amines in both b R and a R, Ν 醯 NJ such as-Ν > Contact with the same base or butyl with the same phase-phase and ketoamine each with its propylamine 0 ethylenediyl ethene printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs, printed as aromatic radicals. f 3) he-N (2 its base and fluorenyl b R amine and fluorene a ethyl amine 7 substituted hydrazone 4) amine 0 ethylbenzene middle N-yl phosphono carboxylic acid aliphatic ester 1 b R And and ethyl-amino N amines such as) r, phenyl-butyric acid, benzene, 4-group T, and -N Bn I-substituted groups are taken from b- and a- Benzene reads NI group 0 and B N such as the group 'Ϊ _ carboxylic acid aldehyde carnaphthyl-aryl is a T b group ORB ί butyl a-RN and talyl amine and 醯 ·

2 / V This paper size applies the Chinese National Standard (CNS) A4 specification (210 X 297 mm) 503237 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 5. Invention Description () (2 5) The substituted amine group, Wherein R a and R b are both aromatic-substituted aliphatic carboxylic acid fluorenyl groups, each of which may be the same or different, such as N, N -diphenylethylfluorenylamino, N-phenethyl-yl 1- (2-benzene (Propanyl) amino and N-phenethylfluorenyl-N- (4-phenylbutylfluorenyl) amino; (26) substituted amino groups, all of which are aromatic-substituted aliphatic carboxylic acid fluorenyl groups and other Ra and 1 ^ is phenylethylfluorenyl-N-benzylfluorenylamino and N-phenylethylfluorenyl-N- (2-naphthylfluorenyl) amino; (27) substituted amino groups, wherein Ra and 1 ^ are both Aromatic carboxylic acid groups, each of which may be the same or different, such as N, N-dibenzylacetamido and benzobenzyl-N- (2-naphthyl) amino. As far as the substituent α is an alkylthio group, it may be a straight or branched Cl-4 alkylthio group, for example, methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutyl Thio, second butylthio and third butylthio. As far as the substituent α is a C6- 10 aryl group, this group may be unsubstituted or substituted with at least one substituent selected from the substituent group. Examples of the unsubstituted aryl group include, for example, phenyl, 1-fluorenyl and 2-naphthyl. This alkyl, alkanoyl group is such that the substituent > 5 is Cl-4 alkyl, Ci-4 alkoxy, halogen atom, hydroxyl, nitro, phenyl or trifluoromethyl or amino group of formula-NRaRb2 Or the amine group and the halogen atom may be as defined and enumerated above with respect to the substituent α &. (Please read the precautions on the back before filling this page)-Binding and binding «Line-14- This paper size applies to China National Standard (CNS) Α4 specifications (210X297 mm printed by the Consumer Standards Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 503237 A7 B7 V. Description of the invention (A) In the case of substituted aryl groups, there is no particular limitation on the number of substituents α appearing, the only limitations are limited by the number of substitutable positions and steric obstacles. Usually 1 to 5 substituents are preferred, 1 to 3 are more preferred and 1 or 2 is most preferred. Examples of such substituted aryl groups include the following: 1) aryl groups are substituted with at least one値 ^ -4 alkyl, such as 4-methylphenyl, 4-ethylphenyl, 4-propylphenyl, 4-isopropylphenyl, 4-butylphenyl, 4-isobutylbenzene , 4-second butylphenyl, 4-third butylphenyl, 4-methyl-1-zeyl, 5-ethyl-1-zeyl, 8-propyl-1-zeyl, 4-Isopropyl-1-naphthyl, 5-butyl-1- # yl, 4-isobutyl-1- # yl, 4-second butyl-1-naphthyl, 4-tert-butyl 1-naphthyl, 4-methyl-2-zeyl, 5-ethyl-2-zeyl, 8-propyl-2- 2-yl, 4-isopropyl -2 -naphthyl, 5-butyl-2-naphthyl, 8-isobutyl-2-naphthyl, 4-second butyl-2-naphthyl or 5-third butyl-2-naphthyl . 2) The aryl group is substituted with at least one Ci-4 alkoxy group, such as 4-methoxyphenyl, 4-ethoxyphenyl, 4-propanyl, 4-isopropoxyphenyl, 4-but P-phenylene, 4-isobutoxyphenyl, 4-second butoxyphenyl, 4-third butoxyphenyl, 4-methoxy-1-zetyl, 5-ethoxy-1-tsai , 8-propoxy-1-zeinyl, 4-isopropoxy-1-naphthyl, 5-butanyl-1-naphthyl, 4-isobutanyl-1-naphthyl, 4- Second butanyl-1-naphthyl, 4-third butoxy-1-naphthyl, 4-methoxy-2-naphthyl, 5-ethoxy-2-naphthyl, 8-propoxy 2-naphthyl, 4-isopropoxy-2-naphthyl, 5-butanyl-2-naphthyl, 8-isobutoxy-2-naphthyl, 4-second butoxy- 2- # based or 5-tert-butoxy-2-naphthyl; -15- This paper size applies to China National Standard (CNS) A4 (210X297 mm) --------- «Packing- -(Please read the notes on the back before filling out this page) Order it 503237 A7 B7 V. Description of the invention (, 〇3) The aryl group is replaced with a halogen atom, such as 4-bromophenyl, 4-chlorophenyl, 4 -Fluorophenyl, 4-iodophenyl, 3-chlorophenyl, 3-fluorophenyl, 3-bromophenyl, 3-iodophenyl, 4-bromo-1-naphthyl, 4-chloro-1- Naphthyl 4-fluoro-1- # yl, 4: iodo-1-naphthyl, 5-chloro-1-naphthyl, 5-fluoro-pyridinyl, 5-bromo-1-naphthyl, 8-l-1-enyl , 4-fluoro-2-zeeki, 4-bromo-2-zeeki, 4-chloro-2-zeeki, 4-iodine-2-leki, 5-mo-2-zeeki, 5- 2-Czechyl, 5-fluoro-2-Ryzyl and 5-iodo-2-Czechyl; 4) Aryl is substituted with hydroxyl, such as 2-hydroxyphenyl, 3-hydroxyphenyl, 4-hydroxyphenyl , 4-hydroxy-1-zekiyl, 5-meryl-1- # yl, 8-hydroxy-1-zekiyl, 4-hydroxy-2-naphthyl, 5-hydroxy-2-naphthyl or 8-hydroxy -2- # group; 5) aryl group is substituted with nitro group, such as 2-nitrophenyl group, 3-nitrophenyl group, 4-nitrophenyl group, 4-nitro-1- # group, 5-nitro group , 8-nitro-1-naphthyl, 4-nitro-2-zeyl, 5-nitro-2-zeyl or 8-nitro-2-ryl; 6) aryl is substituted with phenyl , Such as 3-phenylphenyl, 4-phenylphenyl, 4-phenyl-1-naphthyl, 5-phenyl-1- # yl, 8-phenyl-1-naphthyl, 4-phenyl -2-naphthyl, 5-phenyl-2-naphthyl or 8-phenyl-2-naphthyl; economic Zou Zhong 夬 夬 隼 ¾ 隼 X. Consumption combined with crazy printing S. (Please read the precautions on the back before (Fill in this page) 7) aryl is substituted with trifluoromethyl, such as 3-trifluoromethylphenyl, 4-trifluoro Phenyl, 4-trifluoromethyl-1-naphthyl, 5-trifluoromethyl-1-naphthyl, 8-trifluoromethyl-1-naphthyl, 4-trifluoromethyl-2-naphthyl Group, 5-trifluoromethyl-2-naphthyl or 8-trifluoromethyl-2-naphthyl, 8) aryl is substituted with at least one unsubstituted or substituted amine group, as by unsubstituted amine group Substituents, for example, 2-aminophenyl, 3-aminephenyl, 4-aminophenyl, 4-amino-1- # and 8-amino-2- # and substituted amines Basis, for example: -16- This paper size applies to Chinese National Standards (CNS} M specifications (2 丨 〇X29 * 7mm) Printed by the Department of Shellfish Consumer Cooperation of the Central Standards Bureau of the Ministry of Economic Affairs 503237 A7 B7 V. Description of the invention (i ) An aryl group is substituted with a substituted amine group in which one of Ra and Rb is a hydrogen atom and the other 1 ^ and 1 ^ are alkyl groups, such as 3-methylaminephenyl, 4-ethylaminephenyl, 3- Propylamine phenyl, 3-isopropylamine phenyl, 4-butylamine phenyl or 3-isobutylamine phenyl; ii) aryl is substituted with substituted amine, one of which is a hydrogen atom and the other is aromatic Alkyl, such as 4-benzylaminophenyl, 4- (2-phenylethylamino) phenyl, 4- (1-phenylethylamino) phenyl, 4- (4-phenylbutylamino) phenyl 4- (1-fluorenylmethylamino) phenyl; iii) aryl group is substituted to be substituted amine group, in which one of 113 and 1 ^ is a hydrogen atom and the other Ea * Rb is an aryl group, such as 4-aniline Phenyl, 4- (1-naphthylamino) phenyl; iv) aryl is substituted with a substituted amine, wherein one of Ra and Rb is a hydrogen atom and the other is an aliphatic fluorenyl, such as 4- Formamidine phenyl, 4-acetamidine phenyl, 4-butamidine phenyl, 4-pentamidine phenyl, 4-hexamide phenyl, 4-octylamine phenyl or 4-decamethyl -Aminephenyl; V) an aryl group is substituted with a substituted amine group, one of which is a hydrogen atom and the other Ra and Rb are aromatic-substituted aliphatic fluorenyl groups, such as 4-phenylethylaminophenyl, 4- (4-phenylbutylamidinoamino) phenyl, 4- (6-phenylhexylamido) phenyl, 4-U-methylphenethylamido) phenyl or 4-U, cr -di Methylphenethylamido) phenyl; vi) an aryl group substituted with a substituted amine, wherein one of Ra and Rb is a hydrogen atom and the other is an aromatic fluorenyl, such as 4-benzylamidophenyl, 4- (1-naphthylamino) phenyl or 4- (2-naphthylamino) phenyl; vii) aryl groups are substituted with substituted amine groups, where! Both ^ and ^ are -17-This paper size applies to Chinese National Standard (CNS) A4 (210X29 * 7mm) binding (please read the precautions on the back before filling this page) Printed by the Staff Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs袈 503237 A7 B7 V. Description of the invention (alkyl groups, each of which may be the same or different, such as 4-dimethylaminephenyl, 4-diethylaminephenyl or 4- (N-methylethylamino) phenyl Viii) aryl is substituted with substituted amine, where! One of 3 and 116 is an alkyl group, and the other R a and R b are aralkyl groups, such as 4- (N-ethyl-benzylamino) phenyl, 4- (N-third-butyl- N-benzylamino) phenyl or 4- (N-hexylbenzylamino) phenyl; ix) an aryl group substituted with a substituted amine group, one of 83 and 8 & is an alkyl group and the other 2Ra * Rb is an aryl group, such as 4-U-methyl-N-aniline) phenyl or 4- (N-octyl-N-aniline) phenyl; X) an aryl group is substituted to be substituted, One of them is an alkyl group and the other 113 and ^ are aliphatic fluorenyl groups, such as 4- (propyl-N-ethoxyamino) phenyl or 4- (N-ethyl-N-hexan-amino) benzene Xi) an aryl group is substituted with a substituted amine group, wherein one of Ra and βb is an alkyl group and the other is an aromatic-substituted aliphatic fluorenyl group, such as 4- (N-ethylphenylethylamino) Phenyl or 4- [N-methyl-N- (6-phenylhexyl) amino] phenyl; xii) an aryl group substituted with a substituted amine group, wherein one of Ra and R is alkyl And other 1 ^ and 1 ^ are aromatic fluorenyl groups, such as 4- (N-methyl-N-benzylamido) phenyl or 4- (N-heptyl-N-benzylamido) phenyl; xiii) aryl is substituted with substituted amine, where 1? 3 And 1-13 are both aralkyl groups, each of which may be the same or different, such as 4-dibenzylaminophenyl or 4- [4-benzyl-N_ (2-naphthylmethyl) amino] phenyl; xiv ) An aryl group is substituted with a substituted amine group, wherein one of Ra and Rb is an aralkyl group and the other 1 ^ and 1 ^ are aryl groups, such as 4- (N-benzyl-N--18- The scale is applicable to Chinese National Standard (CNS) A4 * i (210X297 mm) (Please read the precautions on the back before filling this page)

Printed by the Central Bureau of Standards, Ministry of Economic Affairs, Shellfish Consumer Cooperative, 503237 A7 B7 V. Description of the invention (4) Anilino) phenyl or 4- [N- (3-phenylpropylaniline) phenyl; xv) aryl is substituted With substituted amine groups, one of 1 ^ and 1 ^. Is an aralkyl group and the other 1 ^ 3 and 1! 11 > is an aliphatic fluorenyl group, such as 4- (N-benzyl-N-acetamido) phenyl or 4- (N-benzyl-N-pentamidoamino) phenyl; xvi) aryl is Substituted with a substituted amine group in which one of Ra and Rb is an aralkyl group and the other Ra and 1 ^ 15 are aromatic-substituted aliphatic fluorenyl groups, such as 4- (N-benzylphenethyl-amino) benzene Or 4- [N-benzyl-N- (4-phenylbutylfluorenyl) amino] phenyl; xvii) aryl is substituted with substituted amine, one of which is aralkyl and the other 113 and { ^ Is an aromatic fluorenyl group, such as 4- (N-benzyl-N-benzylfluorenylamino) phenyl or 4- [N- (2-phenethyl) -N-benzylfluorenylamino] phenyl; xviii) Aryl groups are substituted with substituted amine groups, all of which are aryl groups, each of which may be the same or different, such as 4-diphenylaminephenyl or 4- [N- (2-naphthyl) -N-aniline] Phenyl; xix) an aryl group substituted with a substituted amine group, one of which is an aryl group and the other 3 and ^ are aliphatic fluorenyl groups, such as 4- (butylpropylacetamido) phenyl or 4- (N-phenyl-N-hexylamino) phenyl; XX) aryl is substituted with substituted amine, wherein one of Ra and Rb is aryl and the other 卩 3 and 卩 5 are aromatic -Substituted aliphatic hydrazone , Such as 4- (N-phenyl-N-phenylethylamino) phenyl or 4- [N-phenyl-N- (4-phenylbutylfluorenyl) amino] phenyl; xxi) aryl is substituted to be Substituted amine groups, in which one of 1 ^ and ^ is aryl and the other 1 ^ and 1 ^ are aromatic groups, such as 4- (N-phenyl- -19-) This paper applies Chinese National Standard (CNS) A4 size (210X297mm) (Please read the precautions on the back before filling this page) i Pack. Order 503237

A B7 indicates that the substitution of the base amines in the fifth is based on the substitution of the base benzene;% »醯) Group 5 benzyl 11 lipids-X ^ NX as if they are not or in the same phase, they can each have b amine and ethyl a Diamino group of di-phenylphenyl group 0 ^ aR. Has been N- to other 0 ^ Μ ^ ^--T group Ν (N aromatic 4. 1 lipid or 11 as the group XX 1 and the ^ 0 family and Lipid a substitutes R for T and its aryl group is arylamine ethylbenzene

Substitute base for amine): Take N-fluorene- (ethyl Π4benzene) such as Γ} Ν V f for aldehyde ethylamine and its _ -------- · Packing— (Please read the notes on the back before filling in this page) 0 Group T lipid group is 11 ethyl and its base-fluorenyl aldehyde butyl is N-b CRI Π 4 ί or a β-based benzyl} ylamine

Amine) V-based X-based aryl is homogeneous b R and a R in which the amine is replaced by •, the substituted group is benzene and the group 0 aliphatic is substituted-fragrant aromatic

Benzene \ n / base amine ethylbenzene di-N with | unradical or fluorene with ethyl phase benzene is N-but C 4 or OR, the base amine in b R and a R is substituted by quilt; Basic benzene is taken by 3 amine amines. — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — —— — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — — Cooperation Du Yin «. Such as or phenyl benzene / amine 0 Benzyl-ϋρ-Benzene ethylbenzene

The substituent is substituted by 11-generation naphthalene and 2-substituted by T group N t -aryl U _vi ethyl XX aminoamino phenylbenzene are substituted by the same amine in b R and a R) Its iso-naphthalene, phase 2-face is-(Fang Ke -N-based each alkane and its aromatic, benzyl is based on N-α 醯 t-based aromatic 4-generation aromatic or is based on the paper standard applicable Chinese national standard ( CNS) A4 (2 丨 0X297 mm) such as aminoaminobenzene or benzene substituted with amine 被 卞 io 503237 A7 B7 V. Description of the invention (· 2) One or more substituents as defined and listed above α. This group (including any substituents) preferably contains 7 to 11 sulfonium atoms. The alkyl portion of the aralkyl group is Ci-5 alkyl ^ Examples of such aralkyl groups include benzyl, 2-benzene Ethyl, 1-phenethyl, 3-phenylpropyl, 2-phenylpropyl, 1-phenylpropyl, 4-phenylbutyl, 1-phenylbutyl, 5-phenylpentyl, p-naphthylmethyl and 2-naphthylmethyl. In the form of substituted aralkyl groups, there is no particular limitation on the number of substituents 々 present, and the only limitations are limited by the number of substitutable positions and steric obstacles. Generally, 1 to 5 痼 substituents as a comparison 1 to 3 is more preferred and 1 or 2 is most preferred. Examples of such substituted aralkyls include the following: 1) Aralkyls are substituted with at least one Ci-4 alkyl, such as 4 -Methylbenzyl, 4-ethylbenzyl > 4-propylbenzyl, 4-isopropylbenzyl, 4-butylbenzyl 4-isobutylbenzyl $ 4-second butylbenzyl, 4-tertiary butylbenzyl 4-methyl 1-naphthylmethyl 9 5-ethyl-1 -naphthylmethyl 8-propyl-1-naphthylmethyl t 4 -isopropyl-1 naphthylmethyl t 5-butyl-1 -zeethymethyl, 4- Isobutyl-1-naphthylmethyl, 4-second butyl-1-zeolyl, 4-tert-butyl-1-naphthylmethyl f 4-methyl + naphthylmethyl 5-ethyl-2 -trimethyl , 8-propyl-2-naphthylmethyl 4-isopropyl-2 -naphthylmethyl, 5-butyl-2 -naphthylmethyl, 8-isobutyl-2 -naphthylmethyl, 4-th Dibutyl • 2-naphthylmethyl or 5-tert-butyl-2- 2-methylmethyl printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) 2) aralkyl Is substituted with at least one Ci-4 alkoxy group, such as 4-methoxybenzyl, 4-ethoxybenzyl, 4-propoxybenzyl, 4-isopropylbenzyl, 4-butylbenzyl, 4-isobutoxybenzyl, 4-second butoxybenzyl, 4-third butoxybenzyl, 4-methoxy-1-naphthalene Methyl, 5-ethoxy-1-naphthylmethyl, 8-propanyl-1-naphthylmethyl, 4-isopropanyl-1-naphthylmethyl, 5-butanyl-1-naphthyl- 21- This paper size is in accordance with Chinese National Standard (CNS) A4 (210X297 mm) 503237 A7 B7 V. Description of the invention (d) Methyl, 4-isobutoxy-1-naphthylmethyl, 4-second butyl Oxy-1-naphthylmethyl, 4-tert-butoxy-1-naphthylmethyl, 4-methylamino-2- # methyl, 5-ethoxy-2-naphthylmethyl, 8-propyl Oxy-2- # methyl, 4-isopropoxy-2-naphthylmethyl, 5-butanyl-2-naphthylmethyl, 8-isobutoxy-2-naphthylmethyl, 4-th Dibutoxy-2-naphthylmethyl or 5-third butanyl-2-fluorenylmethyl; 3) aralkyl is substituted with a halogen atom, such as 4-bromobenzyl, 4-chlorobenzyl, 4 -Fluorobenzyl, 4-iodobenzyl, 3-chlorobenzyl, 3-fluorobenzyl, 3-bromobenzyl, 3-iodobenzyl, 4-bromo-1-naphthylmethyl, 4-chloro-1 -Drug methyl, 4-fluoro-1-naphthylmethyl, 4-iodo-1-naphthylmethyl, 5-chloro-1-naphthylmethyl, 5-fluoro-1-naphthylmethyl, 5-bromo-bu Naphthylmethyl, 8-chloro-1-naphthylmethyl, 4-fluoro 2-naphthylmethyl, 4-bromo-2-naphthylmethyl, 4-chloro-2-naphthylmethyl, 4-iodo-2--2-methyl, 5-bromo-2-naphthylmethyl, 5-chloro 2-naphthylmethyl, 5-fluoro-2-naphthylmethyl and 5-iodo-2-lylmethyl; 4) aralkyl is substituted with a hydroxyl group, such as 2-hydroxybenzyl, 3-hydroxybenzyl, 4-hydroxybenzyl, 4-hydroxy-1-naphthylmethyl, 5-hydroxy-1-naphthylmethyl, 8-hydroxy-1-naphthylmethyl, 4-hydroxy-2-naphthylmethyl, 5-hydroxy- 2- # methyl or 8-hydroxy-2-naphthylmethyl; printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) 5) aralkyl is substituted with nitro, Such as 2-nitrobenzyl, 3-nitrobenzyl, 4-nitrobenzyl, 4-nitro-1-naphthylmethyl, 5-nitro-1-naphthylmethyl, 8-nitro-1-naphthylmethyl Methyl, 4-nitro-2-naphthylmethyl, 5-nitro-2-naphthylmethyl or 8-nitro-2-naphthylmethyl; 6) aralkyl is substituted with phenyl, such as 3-phenylbenzyl Methyl, 4-phenylbenzyl, 4-phenyl-1-zemyl, 5-phenyl-1-zemyl, 8-phenyl-1-zemyl, 4-phenyl-2-naphthylmethyl, 5-benzene 2-naphthylmethyl or 8-phenyl- 2--22- This paper size applies to the Chinese National Standard (CNS) A4 (210X297 mm) Printed by the Labor Standards Cooperative of the State Standards Bureau 503237 A7 B7 V. Description of the invention (/) Naphthylmethyl; 7) Aralkyl is substituted with trifluoromethyl, such as 3-trifluoromethylbenzyl, 4-trifluoro Methylbenzyl, 4-trifluoromethyl-1-naphthylmethyl, 5-trifluoromethyl-1-naphthylmethyl, 8-trifluoromethyl-1-naphthylmethyl, 4-trifluoromethyl -2- # methyl, 5-trifluoromethyl-2-naphthylmethyl or 8-trifluoromethyl-2-zeemethyl, 8) aralkyl is substituted with at least one unsubstituted or substituted amine group, such as Substituted with unsubstituted amine groups such as 2-aminobenzyl, 3-aminobenzyl, 4-aminobenzyl, 4-amino-1-naphthylmethyl and 8-amino-2-naphthylmethyl and Substituted with substituted amine groups, for example: i) Aralkyl is substituted with substituted amine groups, where one of Ra.Rb is a hydrogen atom and the other βa and Rb are alkyl groups, such as 3-methylamine benzyl Group, 4-ethylamine benzyl, 3-propylamine benzyl, 3-isopropylamine benzyl, 4-butylamine benzyl or 3-isobutylamine benzyl; ii) arylalkyl substituted with substituted amine group Where one of ^ 3 and 8 ^ is a hydrogen atom and the other 113 and 1 ^ 13 are aralkyl groups, such as 4-benzylamine benzyl, 4- (2-phenylethylamino) benzyl, 4- (1 -Phenethylamine ) Benzyl, 4- (4-phenylbutylamino) benzyl or 4- (1-naphthylmethylamino) benzyl; iii) aralkyl is substituted with a substituted amine, one of which is a hydrogen atom And the others are aryl groups, such as 4-anilinobenzyl, 4- (1-fluorenylamino) benzyl; iv) the aralkyl group is substituted with a substituted amine group, one of which is a hydrogen atom and the other It is an aliphatic fluorenyl group, such as 4-formamidine benzyl, 4-acetamidine benzyl, 4-butamidine benzyl, 4-tetramethylammonium benzyl, 4-hexamidine benzyl, 4- Octylamine benzyl or 4-undecylamine phenyl; -23- This paper size applies to China National Standard (CNS) A4 * i (210X297 mm) --------- »pack- (Please read the notes on the back before filling out this page) ar -1% Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 503237 A7 _._ B7__ V. Description of the Invention (W) v) The aralkyl group is replaced by Substituted amine groups in which one of Ra and Rb is a hydrogen atom and the other 113 and 1113 are aromatic-substituted aliphatic fluorenyl groups, such as 4-phenylethylamidinobenzyl, 4- (4-phenbutylamidino) Benzyl, 4- (6-phenyl.hexylamino) benzyl, 4-U-methylphenethylamido) benzyl or 4-U, σ- Methylphenethylamido) benzyl; vi) aralkyl is substituted with substituted amine, one of which is a hydrogen atom and the other is an aromatic aldehyde, such as 4-benzylamine benzyl, 4- (1-naphthylamino) benzyl or 4- (2-naphthylamino) benzyl; vii) aralkyl groups substituted with substituted amino groups, all of which are alkyl groups, each of which may be the same or Different, such as 4-dimethylaminobenzyl, 4-diethylaminobenzyl or 4- (N-methyl-N-ethylamino) benzyl; viii) aralkyl is substituted with a substituted amine, One of them is an alkyl group and the other 1 and ^ are aralkyl groups, such as 4- (N-ethylbenzylamino) benzyl, 4- (N-third-butyl-N-benzylamino) benzyl Or 4- (N-hexyl-N-benzylamino) benzyl; ix) aralkyl is substituted with a substituted amine, one of which is alkyl and the other is 113 and! ^ Is an aryl group, such as 4- (N-methyl-N-aniline) benzyl or 4- (N-octyl-N-aniline) benzyl; X) aralkyl is substituted to be substituted amine One of Ra and Rb is an alkyl group and the others & 3 and 1 ^ 13 are aliphatic fluorenyl groups, such as 4- (propyl-N-acetamido) benzyl or 4- (N-ethyl -N-hexylamino) benzyl; 'xi) aralkyl is substituted with substituted amine, where Ra and one are alkyl and the other Ra and! ^ 13 is aromatic-substituted aliphatic fluorenyl group, such as 4- (N-ethyl-N-phenethylamido) benzyl or 4- [N-methyl-bu (6-24- This paper is applicable to China National Standard Rate (CNS) A4 (210X297 mm) (Please read the notes on the back before filling out this page) Pack-Order 503237 Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 5. Invention Description (^) -Phenylhexyl) amino] benzyl; xii) aralkyl is substituted with substituted amine, wherein one of Ra and Rb is alkyl and the other is aromatic fluorenyl, such as 4- (N -formyl -N-benzylamino) benzyl or 4- (N-heptyl-N-benzylamino) benzyl; xiii) aralkyl is substituted with substituted amine, where & is aralkyl Groups, each of which may be the same or different, such as 4-dibenzylaminophenyl or 4- [4-benzyl-N- (2- ^ methyl) amino] benzyl; xiv) aralkyl is substituted with A substituted amine group, one of which is an aralkyl group and the other 1 ^ and 1 ^ are aryl groups, such as 4- (N-benzyl-N-aniline) benzyl or 4- [N- (3- Phenylpropyl) -phenylanilide) benzyl; xv) aralkyl substituted with substituted amine, one of which is aralkyl and Others 1 ^ and 1 ^ are aliphatic fluorenyl groups, such as 4- (N-benzyl-N-acetamido) benzyl or 4- (N-benzyl-pivalamido) benzyl; XV i) The aralkyl group is substituted with a substituted amine group, wherein one of Rb is an aralkyl group and the other Ra and 8 ^^ are aromatic-substituted aliphatic fluorenyl groups, such as 4- (N-benzyl-N -Phenethylamido) benzyl or 4- [H-benzyl-N- (4-phenylbutamidino) amino] benzyl; xvii) aralkyl is substituted with substituted amine, where Ra and Rb One is aralkyl and the other 1 ^ and 1 ^ are aromatic fluorenyl groups, such as 4- (N-benzyl-N-benzylamido) benzyl or 4- [N- (2-phenethyl) -N-benzylamino] benzyl; X viii) aralkyl is substituted to be substituted amine, wherein Ra and Rb are both aryl, each of which may be the same or different, such as 4-diphenylamine Benzyl or -25- (Please read the notes on the back before filling out this page) • !.

、 1T 4 This paper size is in accordance with Chinese National Standard (CNS) 8 4 ^ grid (210X29 * 7 mm) 503237 A7 B7 V. Description of the invention (W) 4- [N- (2-naphthyl) -N-aniline group ] Benzyl; xix) aralkyl is substituted with a substituted amine group, wherein one of Ra and Ib is aryl and the other 1 ^ and 1 ^ are aliphatic fluorenyl groups, such as 4- (N-propyl- N-Ethylamino) benzyl or 4- (N-phenylhexylamino) benzyl; XX) aralkyl is substituted with substituted amine, one of which is aryl and the other is 3 And 1113 are aromatic-substituted aliphatic alkyl groups, such as 4- (N-phenyl-N-phenylethylamino) benzyl or 4- [N-phenyl-N- (4-phenylbutylfluorenyl) amino] benzyl Xxi) an aralkyl group is substituted with a substituted amine group, one of which is an aryl group and the other 1 ^ and! ^ Is an aromatic fluorenyl group, such as 4- (N-phenyl-N-benzylfluorenylamino) benzyl; xxii) an aralkyl group is substituted with a substituted amine group, wherein ^ 3 and paragraph 6 are both aliphatic fluorene Groups, each of which may be the same or different, such as 4-diethylamidobenzyl or 4- (N-butylamido-N-hexaneamido) benzyl; xxiii) arylalkyl substituted to be substituted amino , One of which is an aliphatic fluorenyl group and the other Ra and I ^ b are aromatic-substituted aliphatic radicals, such as 4- (N-ethylfluorenyl-N-phenylethylfluorenylamino) benzyl or 4- ( N-Butyl-N-phenethylamido) benzyl; printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling out this page) xxiv) arylalkyl substituted with substituted amine One of which and Rb are aliphatic fluorenyl groups and the other 2Ra and ^ are aromatic fluorenyl groups, such as 4- (N-ethylfluorenyl-N-benzylamino) benzyl or 4- [M-butylfluorenyl-N- (2-naphthylfluorenyl) amino] benzyl; xxv) an aralkyl group substituted with a substituted amine group, wherein Ra and Rb are both aromatic-substituted aliphatic fluorenyl groups, each of which may be the same or different, such as 4- (-26- This paper size applies to China National Standard (CNS) A4 specification (2 丨 OX297 mm) Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs 503237 A7 B7_ V. Description of the Invention (4) Ν, Ν-diphenylethylamido) benzyl or 4- [N-phenethylamido-N- (4-benzene Butanyl) amino] benzyl; xxvi) aralkyl is substituted with a substituted amine group, where one of R a and R b is an aromatic-substituted aliphatic group and the other Ra and R ^ are aromatic fluorene Group, such as 4- (N-phenethylfluorenylbenzylamidinyl) benzyl or 4- [N-phenethylfluorenyl-naphthylfluorenyl) amino] benzyl; xxvii) aralkyl is substituted to be substituted Amine groups in which Ra and Rb are both aromatic fluorenyl groups, each of which may be the same or different, such as 4-dibenzyl alcoholamine benzyl or 4- [N-benzylfluorenyl-N- (2-naphthylfluorenyl) Amine] benzyl. Derived from indolin, indolin, azindrine, azindolin, oxazolopyridine and oxazolopyrimidine rings, each of which may be substituted with a preferred 1 to 3 fluorene substituent α (which is represented by X) Specific examples include, for example: an indole ring group, such as 3-tritylindol-1-yl, 1-methylindyl-3-yl, 1-methylindyl-2-yl, 1-Ethylindoxy-2-yl, 5-methoxy-1,2-dimethylbenzyl-3-methyl, 5-xiangyl-1-methyl-yl, 1-isopropyl B3I, pyridin-3-yl, 2-ethyl-1-methylindole, 3-dolyl, 5-methoxy-1-methylindole, ifdol-3-yl, 5-hydroxy-1, 2 -Dimethylindino-3 -yl, 5-butoxy-1 -methylindole-3 -yl, 1, 4, 7-trimethylindino-3 -yl, 1, 3- Dimethylindo IT-3-yl, 5-bromo-6-chloro-1 -methylindole B 3-yl, 5-bromoindole-3 -yl, 5-hydroxy-1 -isobutyl Indolin-3 -yl, 5-fluoro-1 -methylindole-2 -yl, 5-hydroxy-1 -methylindole-2 -yl, 4-methylamino-methylindole- 2-yl, 5-bromo-1 -methylindino-2 -yl, 1 -ethyl-5 -nitroindolin-2 -yl, 1,5-dimethylindino-2 -yl, 5--27- This paper is in standard size National Standard (CNS) Α4 specification (2 丨 〇 × 29? Mm) (Please read the precautions on the back before filling out this page) Order Λ Consumer Cooperation of the Central Standards Bureau of the Ministry of Economic Affairs Du printed 503237 A7 _B7_ V. Description of the invention (J ) Amino-1-methylindolin-2-yl, 5-acetamido-1-methylindole-2-yl, 5-benzylamido-1-ethylindole-2- 1-methyl-5-methylamino indol-2-yl, 5-butylamino-1-methyl indol-2-yl, 5- (N-benzyl.fluorenyl-N- (Methylamino) -1-methylindolin-2-yl, 1-methyl-5-anilinindin-2-yl, 5-acetaldehyde indol-2-yl, 5-benzylhydrazone Amino-1-butylindole-2-yl, 4-chloro-1 -methylindole-2 -yl, 3-methoxy-1-methylindolin-2-yl, 6- Fluoro-1-methylindole Ifido-2-yl, 6-chloro-1-ethylindole-2-yl, 6-methylamino-1-methylindole-2-yl, 5,6 -Dimethoxy-p-methylindole "Dor-2-yl, 7-methylindo-Sd-2-yl, 1-methylind-S-5" -yl, 1-butylindin-5-yl , 1-ethylindolin-5-yl, 1-methylindolin-4-yl, 1-isopropylindole-4-yl and butylbutylindole-4-yl; indolinline ring group, 5-Methanyl B Gadoline-1 -yl, 1-methylindolin-2-yl, 1-ethylindolin-2-yl, propylindolin-2-yl, butylindolin-2-yl and 1-isopropylindin-2-yl group; azindole ring groups, such as 1-methyl-7-azindino-3-yl, 1-isopropyl-7-azindolin-3-yl , 1-methyl-7-acridin-2-yl and 1-methyl-6-acidin IT-2-2; azindole acyl ring group, such as 1-methyl-7-acridin Porphyrin-2-yl, 1-ethyl-7-acridinyl-II-Porphyrin-2-yl, 1-isopropyl-7-azindolinyl-2-yl, and 1-butyl-7-azindin Indolin-2-yl; oxazolopyridine ring groups, such as -28- This paper size applies to China National Standard (CNS) A4 (210X29 * 7 mm) (Please read the precautions on the back before filling this page ) > Clothes · Order 503237 A7 _B7_ V. Description of the invention (outside) Printed by the Shellfish Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) 7-methyloxazole and [4, 5-b] pyridin-2-yl, 1-butylimidazolo [4,5-b] pyridin-2-yl, 1-methyloxazolo [4,5-b] pyridin-2-yl, 1 -Propyloxazolo [4,5-b] pyridin-2-yl, 5-chloro-1-. Methylpyrazolo [4,5-b] pyridin-2-yl, 5-methylamino-1.methylimidazo [4,5-1)] pyridin-2-yl, 6,8-dibromofluorene Azolo [1,21] pyridin-2-yl, 8-hydroxyxazolo [1,2-a] pyridin-2-yl, 6-chlorooxazolo [1,2-a] pyridin-2-yl , 2-methyloxazolo [1,2-a] pyridine, 7-yl, 2-ethyloxazolo [1,2-a] pyridin-8-yl, 3-'methyloxazolo [ 5,4-b] pyridin-2-yl, 3,7-dimethyloxazolo C 5, 4-b] pyridin-2-yl, 5-amino-3-methyloxazolo [5,4 -b] pyridin-2-yl, 5-chloro-3-phenyloxazo [5,4-b] pyridin-2-yl, 3-bromo-3-methyloxazo [5,4-b ] Pyridin-2-yl, 3-methyl-6-trifluoromethyloxazo [5,4-b] pyridin-2-yl, 3-isopropyl-6-trifluoromethyloxazolyl [5,4-b] pyridin-2-yl, 3-isopropyl-6-trifluoromethyloxazo [5, 4-b] pyridin-2-yl, 3- (3-chlorobenzyl) Imidazolo [5,4-b] pyridin-2-yl, 3-benzyloxazolo [5,4-b] pyridin-2-yl, 3- (4-azabenzyl) oxazolo [5, 4-b] pyridin-2-yl, 3- (4-phenylbenzyl) oxazo [5,4-b] pyridin-2-yl, 6-bromo-3-methylimidazo [5,4 -b] pyridin-2-yl, 6- -3 -ethyloxazolo [5,4-b] pyridin-2-yl, 6-bromo-3-phenyloxazolo [5,4-b] pyridin-2-yl, 6-chloro-3 -Methyloxazolo [5,4-b] pyridin-2-yl, 3-butyl-6-chlorooxazolo [5,4-b] pyridin-2-yl, 5-methylamino-3 -Methyloxazo [5,4-b] pyridin-2-yl, 3-ethyl-5-methazolo [5,4-b] pyridin-2-yl, -29- Applicable to China National Standard (CNS) A4 specification (210 X 29 * 7 mm) 503237 A7 _B7_ · _ V. Description of the invention (〇) 5 -methylamino-3-propyloxazolo [5,4-b] Pyridin-2-yl, 5-methylamino-3-phenyloxazo [5,4-b] pyridin-2-yl, 3-benzyl-5-methylazolido [5,4-b ] Bttidin-2-yl, 3- (3-aminophenyl) -5-methoxyoxazolo [5,4-b] pyridin-2-yl, 5-hydroxy-3-methyloxazolo [ 5,4-b] pyridin-2-yl, 3-ethyl-5-hydroxyoxazo [5,4-b] pyridin-2-yl, 3-benzyl-5-hydroxyoxazo [5, 4-b] pyridin-2-yl, 3-phenylimidazo [5, 4-b] pyridin-2-yl, 3- (4-chlorophenyl) oxazo [5,4-b] pyridine- 2-yl, 3- (3-chlorophenyl) amido [5,4-b] ohyn-2-yl, 3- (3-methylphenyl Taste and [5,4-b] Yodo-2-yl, 5-chloro-3 (3-aminophenyl) oxazo [5,4-b] pyridin-2-yl, 5-methoxy 3- (3-methylphenyl) oxazo [5,4-b] pyridin-2-yl, 5-hydroxy-3,6-dimethylimidazo [5,4-b] fluorene ratio Pyridin-2-yl, 5-methoxy-3,6-dimethyloxazolo [5,4-b] pyridin-2-yl, 3-methyloxazolo [5,4-b] pyridine -5-yl, 2,3-dimethylxazolo [5, 4-b] pyridin-5-yl, printed by Shelley Consumer Cooperative, Zhongluo Standard Bureau, Ministry of Economic Affairs (please read the notes on the back before filling (This page) 3-ethyl-2-phenyloxazo [5, 4-b] pyridin-5-yl, 2- [2- (3,5-di-tert-butyl-4-hydroxyphenyl) ) Ethyl] -3-methyloxazolo [5,4-b] pyridin-5-yl, 2- (3-chlorophenyl) -3 -methyloxazolo [5,4-b] pyridine -5-yl, 3-methyl-5-phenylthioxazo [5,4-b] oxidin-2-yl, 5-butylthio-3-methylimidazo [5,4-b] Pyridin-2-yl, 3-methyl-5-phenyloxazo [5, 4-b] pyridin-2-yl, 5- (3,5-di-tert-butyl-4-hydroxybenzene Thio) -3-methyloxazo [5, 4-b] pyridin-2-yl, 5-ethoxy-3-methyloxazolyl 5,4-b] pyridin-2-yl, 5-isopropanyl-3-methyloxazolo-30- This paper is applicable to China National Standard (CNS) A4 standard (210X297 mm) 503237 A7 __B7 _ V. Description of the invention (4) The spine-like horseman X. Consumption ftit printed in the spine «. (Please read the precautions on the back before filling this page) [5,4-b] pyridin-2-yl , 5-Ethyloxy-3-methyloxazolo [5, 4-b] pyridin-2-yl, 3-ethyl-5 -benzyl-6-trifluoromethyloxazolo [5 , 4-b] pyridin-2-yl, 7-chloro-3-methyloxazolo [5,4-b] pyridin-2-yl, 7-chloro-3-propyloxazolo [5, 4-b] pyridin-2-yl, 6-hydroxy-3,5,7-trimethyloxazo [5,4-b] pyridin-2-yl, 3,5, trimethyl-6- Nitroxazo [5, 4-b] pyridin-2-yl, 6-amino-3, 5,7-trimethyloxazo [5, 4-b] pyridin-2-yl, 3- Methyl-5-methylaminopyrazolo [5,4-b] pyridin-2-yl, 5-dimethylamino-3 -methyloxazolyl [5,4-b] pyridine-2 -Yl, 5- (N-butylethylamino) -3 -methylimidazo [5,4-b] pyridin-2-yl, 3-methyl-5-anilinopyrazolo [5,4 -b] pyridin-2-yl, 5-benzylamino- 3-methyloxazolo [5, 4-b] ohidin-2-yl, 5- (N -ethyl-N-aniline) -3 -methyloxazolo [5,4-b] pyridine 2-yl, 5-acetamido-3-methyloxazo [5,4-b] pyridin-2-yl, 5-benzylamido-3-methyloxazo [5,4 -b] pyrimidin-2-yl, 3-methyl-6-nitrooxazo [5,4-b] pyridin-2-yl, 6-amino-3-methyloxazo [5, 4-b] pyrene (± pyridin-2-yl, 6-benzylamido-3-methylpyrazolo [5,4-b] pyridin-2-yl, 6-pentamyl-3-yl Oxazolo [5,4-b] pyridin-2-yl, 5-benzyloxy-3-methylimidazo [5,4-b] oh-d 2-yl, 2-xiangyl-3- Methyloxazo [5,4-b] pyridin-5-yl, 2-hydroxy-3--oxazolo [5,4-b] pyridin-5-yl, 2-hydroxy-3-phenyloxazole Benzo [5,4-b] pyridine-5-yl, 2-methylthio-3H-oxazolo [5,4-b] pyridin-5-yl, 3-methyl-2-methylthio Oxazo [5,4-b] pyridin-5-yl, 3-benzyl- 2--31- This paper size applies to China National Standard (CNS) Λ4 specification (2 丨 Ox 297 cm) Central sample of Ministry of Economic Affairs Printed by the Consumer Cooperatives of the Associate Bureau 503237 A7 B7 V. Description of the Invention (^) Butylthioxazole [5,4-b] pyridin-5-yl, 5-tert-butylamino-3-methyloxazolo [5, 4-b] pyridin-2-yl, 5-tert-butylamino-3 -Propyloxazolo [5,4-b] pyridin-2-yl, 3,5,7-trimethyloxazolo [5,4-b] pyridin-2-yl, 3- (3-chloro Phenyl) -5,7-dimethyloxazolo [5,4-b] pyridin-2-yl, 3- (3,5-di-third-butyl-4-hydroxybenzyl) -5, 7-Dimethyloxazolo [5,4-b] pyridin-2-yl, 5-acetamido-3-methylimidazo [5,4-b] pyridin-2-yl, 5-ethyl Fluorenyl-3-ethyloxazo [5,4-b] pyridin-2-yl, 6-methoxy-3-methyloxazo [1,2-a] pyridin-2-yl, 1-methyloxazolo [1,2-a] pyridin-2-yl, 1-butyloxazolo [l, 2-a] pyridin-2-yl; oxazolopyrimidine ring groups, such as 3- Methyloxazo [5,4-d] pyrimidin-2-yl, 3-ethyloxazo [5,4-d] pyrimidin-2-yl, and 3- (3-methylbenzyl) oxazole Among [5,4-d] pyrimidin-2-yl ^ compounds (II), compounds of formula (II) and salts thereof are preferred, where: (A 1) X is indolyl, indolyl, and acryl Indolyl, oxazolopyryl or oxazolopyrimidyl, which is unsubstituted or substituted 1 to 3 substituents α as defined below: The substituent cr is a 4-alkyl group, a Ci-4 alkylamino group, a benzylamino group, a halogen atom, a hydroxyl group, an acetamino group, a phenylthio group, a Cl-4 alkylthio group , Trifluoromethyl, nitro, amine groups of the formula-NRaRb, wherein they are the same or different and each is a hydrogen atom, Ci-8 alkyl, C 7 -u aralkyl, C 6-10 aryl, C iu Aliphatic 32- This paper is applicable to the national standard (CNS > Λ4 specification (2 丨 OX297 mm) (please read the precautions on the back before filling this page) Cooperative printed 503237 A 7% B7 V. Description of the invention () fluorenyl, c 8-12 aryl-substituted aliphatic fluorenyl or C 7-U aryl fluorenyl, C 6-10 aryl is unsubstituted or substituted Substitution with at least one fluorene substituent is selected from the group consisting of substituents Sci-4 alkyl, Ci-4 alkoxy, halogen atom, hydroxy, nitro, phenyl, trifluoromethyl, or NRARb Amine, which! ^ And 1 ^ are as defined above. If 3 and ^ are aryl groups or groups including aryl groups, the aryl group is not itself replaced by a group of the formula-NRa Rb; or C 7-u arane Group is unsubstituted or substituted with at least one substituent selected from the group consisting of substituents; and / or (A2) Y is a gas or sulfur atom; and / or (A3) R is a hydrogen atom, Cjl-4 alkyl, Ci -4 alkoxy or halogen atom; and / or (A4) ο is an integer of 1 to 5; and special compounds in which X is defined as (A1), Y is defined as (A2), R is defined as (A3) and m is as (A4) Definition. The better compound (II) is the compound of formula (II) and its salts, in which:-33-This paper size is applicable to China National Standard (CNS) A4 specification (210X297 mm) (Please read the precautions on the back before filling this page )

503237 A7 B7 V. Description of the invention (μ) (B u X is indino, indolinolinyl, oxazolopyridyl or oxazolopyrimidinyl, which is unsubstituted or substituted with 1 to 3 as defined below Substituent α: Substituent α is Cl-4 alkyl, Ci-4 alkanoyl, benzyloxy, halogen atom, hydroxyl, ethanoyl, phenylthio, Cl-4 alkylthio, trifluoromethyl Group, nitro group, amine group of formula-NRaRb, wherein Ra and Rb are the same or different and each is a hydrogen atom, Ci-8 alkyl group, C 7_uaralkyl group, C 6-10 aryl group, C i- u aliphatic fluorenyl, C8-12 aryl-substituted aliphatic fluorenyl or (^ 7_u aryl fluorenyl, C 6-10 aryl which is unsubstituted or substituted with at least one substituent selected from substituents > 8. The substituent point is a ^ -4 alkyl group, a Ci-4 alkoxy group, a halogen atom, a hydroxyl group, a nitro group, a phenyl group, a trifluoromethyl group or an amine group of the formula-NRaRb, wherein Ra and Rb are as defined above, or C7-: ^ aralkyl which is unsubstituted or substituted with at least one substituent selected from the substituents; and / or printed by the Shellfish Consumer Cooperative of the Central Samples Bureau of the Ministry of Economic Affairs *. (Please read the notes on the back before filling (This page) (B2) Y is Atoms; and / or -34- This paper size applies to China National Standards (CNS) Λ4 specifications (2 丨 〇297297 mm) 503237 A7 B7 V. Description of the invention ((B3) R is a hydrogen atom, C!-4 alkane Group, Ci-4 alkanoyl group or halogen atom; and / or (B4) hi is an integer of 1 to 5; and special compounds wherein X is defined as (B1), Y is defined as (B2), and R is as (B 3 ) And m is as defined in (B 4). Still more preferred compound (II) is a compound of formula (II) and a salt thereof, wherein: (C 1) X is indolinyl, indolinolinyl or oxazolopyridyl , Which is unsubstituted or substituted with 1 to 3 substituents σ as defined below: Substituent CT is Ci-4 alkyl, Ci-4 alkoxy, benzyloxy, halogen atom, hydroxyl, ethoxy group , Phenylthio, Ci-4 alkylthio, trifluoromethyl, nitro, amine group of the formula-NRaRb, where they are the same or different and each is a hydrogen atom, 8 groups, C7-11 aromatic groups, C6 -10¾ group, Cl-11 aliphatic fluorenyl group, C8-aryl-substituted aliphatic fluorenyl group or C7-with aromatic group, C6-10 aryl group is unsubstituted or substituted with 1 to 3 substituents Self-substituting cold, the substituent 々 is Ci-4 alkyl, Ci -4 alkane group, halogen atom f ridge% (please read the notes on the back before filling this page), hydroxyl, nitro, phenyl, trifluoromethyl or amine group of formula-NRaRb, of which R3 and Rb As defined above, or C 7 -u aralkyl which is unsubstituted or substituted with at least one substituent selected from the group consisting of substituents; and / or -35- This paper applies the Chinese National Standard (CNS) A4 standard (2 丨 0X297)} Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 503237 A7 _B7_ V. Description of the invention () (C 2) Y is a gas atom; and / or (C4) R is a hydrogen atom, a methyl group, An ethylenyl group, a fluorine atom or a chlorine atom; and / or (C5) m is an integer of 1 to 5; and special compounds in which X is defined as (C1), Y is defined as (C2), as defined in (C3), and R is as (C4) is defined and ffi is defined as (C5). Still more preferred compound (II) is a compound of formula (II) and a salt thereof, wherein: (D1) X is an indolinyl group or an oxazolopyridyl group, which is unsubstituted or substituted with 1 to 3 as defined below Substituent ct: Substituent a. Ci-4 alkyl, CU-4 alkoxy, benzyloxy, halogen atom, phenylthio, Ci-4 alkylthio, trifluoromethyl or phenyl; (D 2 ) Y is a gas atom; and / or (D 3) ^ is sulfur; and / or (D4) R is a hydrogen atom or a methyl group; and / or (D5) π is an integer of 1 to 5; and particularly a compound thereof X is defined as (D1), Y is defined as (D2), Y + is defined as (D3), R is defined as (D4) and m is defined as (D5). -36-This paper size is in accordance with Chinese National Standard (CNS) A4 (210X297mm) I ^ installed '_ _ order (please read the precautions on the back before filling this page) Central sample rate bureau of the Ministry of Economic Affairs Cooperative seal «. 503237 A7 B7 V. Description of the invention (M) The best compound (II) is a compound of formula (II) and its salt, where (E 1) X is oxazolopyridyl, which is unsubstituted or Substituted with 1 to 3 cr as defined by cr: Substituent α is methyl, ethyl, isopropyl, methoxy, ethoxy, propoxy, isopropoxy, benzyloxy, fluorine Atom, chlorine atom, phenylthio, methylthio, ethylthio or phenyl; and / or (Ε2) Υ is a gas atom; and / or (Ε3) Υ 1 is a sulfur; and / or (Ε4) R is Hydrogen atom; and / or (E 5) m is an integer of 1 to 5; and special compounds in which X is defined as (E1), Y is defined as (E2), as defined in (E3), R is defined as (E4) and m As defined in (E5). The compound (I) or (II) each contains one base in its molecule, and therefore can be converted into a salt by a conventional method and an acid. There is no restriction on the nature of the salt, as long as the compound is used in medicine It is pharmacologically acceptable, that is, it is non-lower or less tolerated than the parent compound, and it is not more toxic or more toxic not allowed. However, when this compound is used for non-medical purposes, such as intermediates in the preparation of other compounds, even this restriction does not apply, and there is no restriction on the nature of the salts formed. Examples of such salts include: with mineral acids, other than halogen acids (such as hydrofluoric acid, hydrobromic acid, hydroiodic acid or hydrofluoric acid), nitric acid, peroxyacid -37- Standard (CNS) A4 specification (2 丨 0X297 mm) " (Please read the precautions on the back before filling this page)

503237

AJ ___ BJ_ 5. Description of the invention (K), salts of sulfonic acid, sulfuric acid or phosphoric acid; salts with low-alkane sulfonic acids, such as methanesulfonic acid, trifluoromethanesulfonic acid or ethanesulfonic acid; and aromatic sulfonic acids, Such as benzenesulfonic acid or p-toluenesulfonic acid salts; with organic carboxylic acids such as acetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, benzyl acid, mandelic acid, Salts of ascorbic acid, lactic acid, gluconic acid or citric acid; and salts with amino acids such as glutamic acid or aspartic acid are preferably pharmaceutically acceptable salts. The compound (I) or (II) can be converted into a salt by a conventional method with a base. Examples of such salts include: salts with alkali metals, such as sodium, potassium, or lithium; salts with alkaline earth metals, such as barium or calcium; and salts with other metals, such as magnesium or aluminum. Pharmaceutically acceptable salts are preferred. The compound of the formula (II) of the present invention has various isomer forms β due to the occurrence of asymmetric sulfonic atoms. Therefore, when the indolinoline or azindolino ring is substituted at the 2 or 3 position, The master atom is asymmetric, and the sulfon atom at the 5-position is asymmetric. Although these compounds are represented by a single molecular formula (I) or (II), the present invention includes the seal of the Li Ma employee consumer cooperative in the Ministry of Economic Affairs «-(Please read the precautions on the back before filling this page), Isomeric isomers and mixtures, including their racemic hydrazones and isomers that can exist in this mixture in any ratio. When stereospecific synthesis techniques are used or optically active compounds are used as starting materials, they can be directly prepared. Isomers; on the other hand, if a mixture of isomers is prepared, individual isomers can be obtained by traditional analytical techniques. Compounds of formula (I) or (II) can exist in various tautomeric forms as shown in the following schemes ex, / 3, respectively; _-38-_ This paper is in accordance with the Chinese National Standard (CNS > Λ4 Specification (2 丨0X297 mm) " 503237 A7 B7 V. Description of the invention) Du Yinye

(Please read the precautions on the back before filling in this page) · Binding This paper size applies the Chinese National Standard (CNS) Λ4 specification (2IOX 297) 503237 A7 B7 V. Description of the invention (π)

A

(Please read the precautions on the back before filling out this page.) In formula (I) or (II) above, all its tautomers and the equal or non-equivalent mixtures of these tautomers are represented in one formula. Therefore, all such isomers and mixtures of these isomers are included in the present invention. Printed by the Central Standards Bureau of the Ministry of Economic Affairs, Shellfish Consumer Cooperatives. Moreover, the present invention also includes all solvates of the compounds of formula (I) or (II) and their salts, such as hydrates, where the opposite compounds can form a solvate . The present invention also includes all "prodrugs" which can be metabolized into a compound of formula (II) or a salt compound thereof in a living mammal ". A 40- this paper is suitable for the standard / WM furniture (CNS) Λ4 present (2 丨 0297mm) 503237 A7 B7 V. Description of the invention () The compounds of the present invention can prepare various types of compounds known in the art Process method. For example, it can be prepared by the following reaction schemes A and B including the last heterocyclic compound (II):

Reaction Scheme A 0— (CH2) —Halo (III)

-Packing · (Please read the precautions on the back before filling this page) Step A1 Alkali Q 1 (ch2) 『

Order Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs Step A2 X— (CH2) —

This paper size applies to Chinese National Standard (CNS) A4 (210X297 mm) Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 503237 A7 B7 V. Description of the invention () In the above formula: X is as defined above, but preferably 较佳Zolopyridyl or imidazo! Syndrome; Q, Y, Yf, R and id are as defined above; H a 10 is a halogen atom. Step A1 In step A1, the compound of formula (I) is prepared by reacting a compound of formula (I I I) with a compound of formula (IV) in the presence of a base. There are no particular restrictions on the basic nature used, and any base commonly used in this type of reaction can be used. Examples of such bases include: inorganic bases, such as hydrides (such as hydrogenated pins or potassium sulfide) and sulfonates (such as potassium or sodium sulfonate); and organic bases, such as triethylamine. The reaction is generally and preferably performed in the presence of a solvent. There is no particular limitation on the nature of the solvent used, as long as it does not adversely affect the reaction or the reagents used and can dissolve the reagents to at least some extent. Examples of suitable solvents include: hydrocarbons, which are aliphatic or aromatic, such as benzene, toluene, xylene, hexane or heptane; ethers, such as diethyl ether, tetrahydrofuran or dioxane; ammonium compounds, such as dimethyl Methylformamide, dimethylacetamide, or hexamethyltriamine phosphate; and any two or more of these solvents. The reaction can be performed at a wide range of temperatures, and the present invention does not determine the precise reaction temperature. Generally, it is convenient to carry out the reaction under ice-cooling to heating, such as the reflux temperature of the reaction mixture, and the reaction time is also extensive -42. This paper size applies to China National Standard (CNS) A4g (210X297 mm) gutter ( (Please read the notes on the back before filling this page) 503237 A7 B7 V. The description of the invention (W) is different, depending on many factors, mainly depending on the reaction temperature and the nature of the reagents and solvents used. However, as long as the reaction is performed under the above-mentioned preferred conditions, a period of from 0.5 hours to several days is usually sufficient. The reaction is best performed by cooling or heating or at room temperature in the presence of sodium hydride or a mixture of at least one amidine and at least one other organic solvent in the presence of sodium hydride for 1 to 1 hour. Compounds of formula (I), which are prepared therefrom, are novel compounds and are important intermediates in the preparation of compounds of formula (I I) of the invention. Step A2 In step A2, the compound of formula (I I) is prepared by one of the following two methods (a) and (b). Step A 2 (a) The compound of formula (11) can be obtained by making the compound of formula (I), where Q is low (please read the precautions on the back before filling out this page). Alkoxy m group> is prepared by reacting with a 2, 3-diamino pyridine derivative or a 4, 5- diamino pyrimidine derivative. It is preferred that Q has a low alkane m group with a total of 2 to 7値 m atom (that is, the alkane group has 1 to 6 fluorene atoms), and may be straight or branched. Examples of such groups include methoxym group, ethyl group, m group, propyl group, m group, and isopropyl group. m group? butane m group 9 isobutane carbonyl group second butoxy m group > third butane m group group pentoxy m group iso group m group 9 neopentyl group carbonyl t 2-methyl butane group m Radicals »1-ethylpropane m radical t 4-methylpentane m radical $ 3-methylpentanyl m radical * 2-methylpentanyl radical 1-methylpentanyl radical m 3, 3 -Dimethyl butane carbonyl f 2, 2-Dimethyl butane carbonyl m » 1, 1--43- The standard of this paper is applicable to Chinese National Standards (CNS). Λ4 is present (2 丨 OX 297mm). Lost in Qilang ¾ members M consumption combined i ± s-ft 503237 A7 B7 V. Description of the Invention (^) Dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 1,3-dimethoxybutoxy tearyl, 2, 3-dimethoxybutoxycarbonyl, 2-ethyl Butane carbonyl, hexyl carbonyl and isohexyl chlorocarbonyl. Among them, Cl-4 alkyl carbonyl is preferred, and methoxycarbonyl, ethylchlorocarbonyl, propanecarbonyl, isopropylglass, butanecarbonyl and isobutanecarbonyl are preferred, and the most preferred are methylchlorocarbonyl and Ethyl carbonyl. The reaction is generally and preferably performed in the presence of a solvent. There is no restriction on the nature of the solvent used, as long as it does not adversely affect the reaction or the reagents used and can dissolve the reagents to at least some extent. Examples of suitable solvents include: hydrocarbons such as benzene, toluene, xylene, hexane, or heptane; solvents such as diethyl ether, tetrahydrofuran, or dioxane; ammonium solvents such as dimethylformamide, dimethyl Acetylamine or hexamethyl phosphate triamine; alcohols such as methanol, ethanol or butanol; acids such as acetic acid or propionic acid and a mixture of any two or more of these solvents. The reaction can be performed at a wide range of temperatures, and the present invention does not strictly determine the precise reaction temperature. Generally, it is convenient to carry out the reaction at the reflux temperature of the heating reaction mixture, and the time required for the reaction varies widely, depending on many factors, mainly depending on the reaction temperature and the nature of the reagents and solvents used. However, as long as the reaction is performed under the above-mentioned preferred conditions, a period of 3 hours to several days is usually sufficient. The reaction is best performed in the absence of a solvent at a temperature of 50 ° C to 150 ° C for 5 hours to 2 days. Step A 2 (b) As another method, the compound of formula (II) can be obtained by letting a compound of formula (I) wherein Q is a methyl group, in the first stage with 2, 3-diaminopyridine. The size of this paper is in accordance with the Chinese National Standard (CNS) A4 (210X297 mm) (please read the precautions on the back before filling in this page) Λ Binding 503237 A7 B7 V. Description of Invention (W) Biological or 4, 5- The diaminopyrimidine derivative is reacted, and then the product is prepared by treating the product with a gasifying agent in a second stage. The reaction is generally and preferably performed in the presence of a solvent. There is no particular limitation on the nature of the solvent used, as long as it does not adversely affect the reaction or the reagents used and can dissolve the reagents to at least some degrees. Examples of suitable solvents include: hydrocarbons, which may be aliphatic or aromatic , Such as benzene, toluene, xylene, hexane or heptane; ethers, such as diethyl ether, tetrahydrofuran or dioxane; amines, such as dimethylformamide, dimethylacetamide or hexamethyl Triamine phosphate; alcohols, such as methanol, ethanol, or isopropanol; acids, such as acetic acid or propionic acid; such as fluorene, such as dimethylimide; and a mixture of any two or more of these solvents. The reaction can be performed at a wide range of temperatures, and the present invention does not determine the precise reaction temperature. Generally, it is convenient to carry out the reaction at about room temperature or heating, such as the reflux temperature of the reaction mixture, and the time required for the reaction varies widely, depending on many factors, mainly depending on the reaction temperature and the nature of the reagents and solvents used. However, as long as the reaction proceeds under the above-mentioned preferred conditions, a period of from 1 hour to several days is usually sufficient. Printed by the Huangshuang Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (please read the notes on the back before filling this page) The product is then treated with the chlorinating agent in the second stage. There is no difference in the nature of the gasifier used Restriction, and any gasifier commonly used in this type of reaction can be used. Examples of such gasification agents include live iodine, silver gasification, and lead tetraacetate. Of these, iodine β is generally treated with a gasification agent and is preferably performed in the presence of a solvent. There is no particular restriction on the nature of the solvent used, as long as it does not adversely affect the reaction or the reagents used and can dissolve the reagents to at least some extent. Appropriate -45- This paper size is in accordance with Chinese Standards (CNS) Α4 is present (2! 〇 χ2 公公 f > 503237 A7 B7 V. Description of the invention (such as) Category fine _ It is determined as the best combination of the best The use of the agent to dissolve the essence and use it, so that the progress of the middle and lower steps of the first paragraph of the scope of the scope is broadly included in Bao Keli, the agent should be anti-solubilizing, the temperature should be 0, and the anti-reflective line should be advanced. Resugar is considered more than it is, and it is not the same. The breadth is also the same as the time. The need to be sure is enough to meet the needs of the normal backcompass, and the natural number C is the timing. The small-scale agent, the strip and the test piece under the agent should be used to make it better than what is described in the above steps and walk into the chemical compound in the chemical I) base {Protective type in the base armor Its base ester protection is divided into two groups based on the predecessor-alkane example ffl 2-yl-1, 1, and the base protection group is based on the basic oxygen. This is the second example of the methyl methyl oxide. Base reduction of 2 I alkylene oxides (please read the precautions on the back before filling this page) and base In addition metallocene two side-shift system transfer method known in the 7 ^ 0 alkoxy two cooked at this 3-1, can, Paul protecting group A group 0 [pi ί. The formula is based on 2-such as the example of combining chemical contact 1Γ and S, and then the upper part Γ〇 G, using ve as ti iiec to protect ot to Γ η: system ee pass Gr at 3 = agent T to protect the already recorded components The sermon and this two things, or printed by the Central Bureau of quasi-Ministry of Economic Affairs of the People's Republic of China Shellfish Cooperative Co., Ltd. printed the winter paper. ch2) ht-y

N〇2 Step B2 R V. Description of the invention (^)

Reaction scheme B Q— (CH2) —Halo + HY—N02 Step Bl

(III) R (V) (VI) (Please read the notes on the back before filling this page)

Q- (CH2) E ~ Y

nh2 — 63-R (VII) Q— (ch2) 『y

COOK -5 (VIII) R Halo ’

Step B4-h2n-c—nh2 Y Printed by the Shellfish Consumer Cooperative of the Central Sample Bureau of the Ministry of Economy Q— (ch2) ht-y

x- (CH2) srY step B5

R rv ^^ NH (II) I The paper size is common Chinese National Standard (CNS) A4 specification (2 丨 0X297 mm) -47-503237 A7 B7 V. Description of the invention (^) In the above formula, Q, Y, Y ', lT,) (, Halo and ίο are as defined above; Step B1 In Step B1, the compound of formula (VI) is prepared by reacting a compound of formula (III) with a compound of formula (V) and a base. This reaction is basically It is the same as described in Step A1 of Reaction Scheme A, and can be performed using the same reagents and reaction conditions. Step B2 In Step B2, the compound of formula (VII) is prepared by reducing the compound of formula (VI). Reaction This can be carried out by conventional catalytic hydrogenation or by using any reducing agent capable of reducing nitro, such as zinc-acetic acid or tin-hydrochloric acid. Step B3 In step B 3, the compound of formula (VIII) is borrowed The conditions for preparing the reaction by subjecting the compound of formula (VII) to a Meerwein arylation reaction are well known and similar to those shown in Japanese Patent Laid-open Application No. 55-22657 or S. Oae et al .; Reported by Bull.Chem. Soc. Japan, 53, 1065 (1980). Step B4. Fei Cooperative Press «. (Please read the notes on the back before filling this page) In step B4, the compound of formula (I) is obtained by reacting a compound of formula (VIII) with P or sulfur P and then hydrolyzing the product. The conditions used in this reaction are well known and similar to those shown in Japanese Patent Laid-Open Application No. 55-22657. Step B5 In step B5, the compound of formula (II) is derived from compound (I) Step-48- This paper size is made according to the Chinese National Standard (CNS) A4 specification (210X297 mm) 503237 A 7 B7 V. Illustrated invention (A (a) and A (b)). This reaction is complete In the above steps, the same reagents and reaction conditions can be used. In the above steps, if desired, the products of each step can be recovered from the reaction mixture in a conventional manner at the end of each reaction, and if necessary, the obtained The compounds can be refined in conventional ways, such as by column chromatography, recrystallization, reprecipitation, or similar well-known procedures. An example of such techniques includes: adding a solvent to the reaction mixture; extracting the desired compound ; And will eventually dissolve The solvent removes the solvent from the extract. The obtained residue can be purified by silica gel or similar adsorbent column chromatography to obtain the desired compound as a purified sample. Examples of the specific compound (II) are listed in the following formula (I -1) to (Bu 2): (Please read the notes on the back before filling this page) RX— (CH2) E—

(1-1) Consumption of employees of the Central Bureau of Standards of the Ministry of Economic Affairs, \ R X— (ch2) —

(1-2) -49- • The dimensions are applicable to the Chinese National Standard (CNS) A4 specification (210X297 mm) 503237 A7 B7 V. Description of the invention () Chinese-I Formula 上 The above formula: Yu Yu Guan Guan Yu Yu Yu Ding- ο 0 Substitute the table for the formula is listed in the following table 1, so that 0 in the table 2 is based on butyl butyl fluorenyl butyl triyl propyl propyl is ethyl isobutyl benzyl ethyl toluene Isopropyl I --------- 0 — ^-(Please read the notes on the back before filling this page) Order

II Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs This paper is sized to the Chinese National Standard (CNS) Α4 (210X297 mm) 503237

A B Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs

(Please read the precautions on the back before filling this page) This paper size is applicable to China National Standard (CNS) A4 specification (210X297 mm) 503237

A B7 Explanatory Note% Five Continued / IV 1X Form Printed by the Shellfish Consumer Cooperative of the Central Sample Bureau of the Ministry of Economic Affairs «-

(Please read the precautions on the back before filling this page) This paper size applies the Chinese solid standard "CNS" Λ4 specification (2 丨 0X297 mm) «52- 503237 A7 B7 V. Description of the invention U4) Table 1 (continued) -1 sound _ t Li Wu ** mouth exhaustion C Xiao tv * take Jtpi number XY m R 1-16 λβ o I II 1-17 Me Me s 4 Cl 1-18 _ / Me o 3 OH 1-19 Βκγ ^ \ / 1 Me s 2 Bu 1-20 Br \ ^ \ / XX / 0 5 H 1-21 H〇Y ^ \ / iBu 0 1 H 1-22 0 1 H隼 （CNS） AOl （2 丨 OX 297 public holiday） -53- (Please read the precautions on the back before filling this page) 503237

A

7 B V. Description of the invention (4Λ) Table 1 (continued) Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs ¾ No. X Υ m R 1-23 clxCTi 1 Me υ 1! 1 1-24 ΗΟγ ^ χ—— person 1 Me 0 1 H 1-25 0 1 H 1-26 0 1 H 1-27 1 〇2Νγ ^ —_ 1 AXλλ 0 1 H 1-28 1 Me 0 1 H 1-29 AXλλ 0 IH National Standards (CNSM4 is now < 210/297). (Please read the precautions on the back before filling out this page.) -54- 503237 5. Description of the invention (“) Table 1 (continued) c M * AT P £卩 See number XY ni R 1-30 AcHNN ^ n χλΛ Me 0 1 li 1-31 〇 丄 ^ I Rt 0 1 H 1-32 Η υ ^ Λ 1 Me 0 1 H 1-33 Η Βιι-ίί Human i Me 0 1 H 1-34 Me Bz_N \ r ^ \ Human 1 Me 0 1 H 1-35 HP "Ah, 1 Me 0 1 H Paper size 4 Chuanzhong" M 家 螵 隼 (CNS) Λ4 Specification (2丨 OX 2mm) (Please read the notes on the back before filling in this page)

, TT 503237 A7 B7 V. Description of invention U〇 Table 1 (continued)

In the Ministry of Economy, the sample horseman X consumer cooperative seal U number XY m R 1-36 ACHNY ^ s 1 Η s 2 Me 1-37 ° '" " to 1 Πυ o Λ NieO 1-38 Cl X 1 Me 0 1 H 1-39, OMe person 1 Me 0 1 H 1-40 _ person 1 Me 0 l H 1-41! Et 0 2 Cl M2 1 Me 0 1 H This paper size Tongzhou China National Standard (CNS) Λ4 Specifications (210X297 mm) -56 " (Please read the precautions on the back before filling this page) 503237

TB V. Description of the invention () Table 1 (continued) Printing Co., Ltd. of the Consumer Cooperatives of the Central Sample Bureau of the Ministry of Economic Affairs XY IU \\ 1-43 Me〇 ^ \ Me0 ^ S people Me 0 4 H 1-44 〇1 people MeO s s I li 1-45 ΌΦ A 0 1 H 1-46 Όφ Me 0 l H 1-47 / 丨 1 Bu 0 2 H 1-48 s 1 Me 1-49 xt? Mountain e 0 4 Me paper size Applicable to China National Standards (CNS) A4 «L (210X297mm) -57- (Please read the notes on the back before filling out this page) 503237 A7 B7 V. Description of Invention (4S) Table 1 (Continued) Ministry of Economic Affairs Printed by the Central Bureau of Standards and Industry Cooperatives »Edited XY m R 1-50 Λ 1 Η 0 1 H 1-51 Λ 1 Me o 1 \ H 1-52 0 i Me 0 2 H 1-53 rS 1 iPr 0 2 Me 1-54 rVi Bu s 3 H 1-55 0 1 Me 0 I McO The paper size is common Chinese National Standard (CNS) A4At grid (2 丨 〇 / 297 cm) -58- (Please read the back first Please note this page and fill in this page again) 503237 A7 B7 V. Description of invention 9) Table 1 (continued) No. XY m R 1-56 Λ ~ ί ώ β s 1 H 1-57 Or1 1 ο 2 H 1-58 Me0x < ^ N w 1 0 4 Me 1-59 _ 0 1 H 1-60 i ^ sN_ person 1 H 0 2 H 1-61 〇Λ s 3 H 1-62 0 1 H遢 Use Chinese «Home Standard (CNS) A4 (2 丨 0X297mm) -59- (Please read the precautions on the back before filling out this page) I Pack-Order 503237 A7 B7 V. Description of Invention (⑺) Form 1 (Performance) Printed by the Consumer Cooperatives of the Central Bureau of Standards, Ministry of Economic Affairs ¾ Nitrile XY ni R 1-63 [^ × _ 1 Me 0 2 H 1-64 1 Me o! F 1-65 _ 1 Me sl H 1-66 1 Et 0 1 H 1-67 _ person 1 Pr 0 2 MeO 1-68 _ 1 Bu 0 IH 1-69 _ 1 Me s. 5 H This paper size applies to China's "House Standard 隼 (CNS) A4 Specification (2 丨〇 Dog 297 mm) -60- (Please read the precautions on the back before filling in this page)

1T 503237 A7 B7 V. Description of the invention (d)

Achievements C -1; Table I Consumption Cooperation between Mongolian and Mongolian Employees in the Ministry of Economic Affairs

e (Please read the notes on the back before filling this page)

, 1T 503237 A7 B7 V. Description of the invention (r >

Continued C 1 Form I Printed by the Ministry of Economic Affairs' Consumer Cooperatives

(Please read the precautions on the back before filling out this page) Λ Clothing · Order 503237 A7 B7 V. Description of the invention (with Γν 1 table

Wood Paper Standards Shizhou China National Standards (CNS) Λ4 Specification (2 丨 0X297mm) (Please read the precautions on the back before filling this page) ¥ Order-63- 503237 A7 B7 V. Description of Invention (w) Form 1 (continued) Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs «.

(Please read the notes on the back before filling this page) ._year

, TT -64- 503237 (Μ Β V. Description of the invention (β) Table 1

Continued C

X γ m-

IR 1-103

N

I Me ο 2

H 1-104

N

-N ο 2 Η N- 1-105

N

-N ο 4 Π N- (Please read the notes on the back before filling this page) 1-106 N- ΊΤ ο Η 1-107

CU ο 2 ΙΗ [-108

ο Η [-109

S 印 Consumer Cooperative Cooperatives, Central Provincial Bureau of Economic Affairs, Ministry of Economic Affairs ft 1-110 .111

CkN ^ N- ο ο Chinese translation of this paper avoids the use of Chinese country names (CNS) Α4 坭 格 (2 丨 0X297mm) -65 «Η Η 503237 A7 B7 V. Description of the invention (H) Table 1 (continued) xymr number «5C-- (Please read the notes on the back before filling out this page)

1-116 N-

N Me

O Η 1-117 s

H

N Me 1-118

A N-

O

H Printed by the Consumer Cooperatives of the Central Procurement Bureau of the Ministry of Economy fcN- 1-119 [-120 N.

I

O

Me N-

N Et

O

MeO

-66- The size of this paper is applicable to Chinese National Standards (CNS) Λ4 is present (2 丨 〇〆297 mm) 4 503237 A7 B7 No. XY m R M21 CXX k 0 1 H 1-122 Γ ^ Ίΐ—Ν, person Ν 人 0 1 H 1-123 ζχχ Me 0 3 H 1-124 Me Γ ^ Γ——N 义 N 人 άβ 0 1 H 1-125 0 1 H 1-126 Γ ^ Ί ~ N, c 丨 everyone 0 1 H 1-127 j〇nc 丨 Eight V people Ph 0 3 H 1-128 / νχ 8 into A Me 0 1 H Paper ruler / t Applicable t country multinational standard (CNS) Λ4 specification (2 丨 0 > < 297 mm) (Please read the notes on the back before filling out this page), 1T -67- 503237 A7 B7 V. Description of the invention (β) Table 1 (continued)

Me ----------- # 篆-(Please read the notes on the back before filling this page) M31 1-132 1-133

Ν Ν I Βζ • Ν

Ο Ο Ο 4 Η Η Η ΊΤ Printed by Shellfish Consumer Cooperative, Central Bureau of Standards, Ministry of Economic Affairs 1-134 1-135

〇 〇 This paper is suitable for China Yanjia Standard (CNS) Λ4 size (2Ι〇κ 297mm) Η Η 503237

A 7 Β V. Description of the invention (η) Table 1 (Performance χ γ m-

R .136

Ν Ν I β-PhBz

ο .137 [-138 1-139 1-140 [-141 1-142

Br

Ν ΝI Ph -Ν

Ν-I Me

-Ν Λ X Λ MeO Ν ΝI Me

ο Η Η (Please read the notes on the back before filling this page)-Binding

S ο ο ο Η Η Η This paper size is applicable to China's national standard (CNS > Λ4 spot (2 丨 OX 297 mm)-69- 503237 Α7 Β7 V. Description of the invention Table 1 (continued) No. 1-143 1-144 1-145 [-146 .147

X

Y m

R

MeO

McO

MeO

MeO

MeO

Ο Ο Π Η Η Η Η 消费 The Ministry of Economic Affairs t-clip sample bureau staff consumption cooperation printing

The winter paper scale is applicable to China's national standard (CNS > M this grid (2Ιϋκ 297)) 503237 A7 B7 V. Description of the invention ("Table 1 (achievement)

X

Y m-

R 1-150 1-151

Me o Η [-152

Mxc m-cik

o Η (Please read the precautions on the back before filling out this page) 装 · [-153

o 订 Order 1-154 -N ho Renren Nren I Et

o Η 1-155 Jun Jilang 4-ya licking 隼 members. 11 ¾ fee together 咋 fl. Medium. 156 • 157

-N N I Bz

o o Η Η

-N

N I Me

〇A 3 Η The paper size of the table is applicable to the national standard of the country (CNS) Λ4 grid (210X297 cm) 503237 A7 B7 V. Description of the invention (k) 73 Table 1 (continued) Ministry of Economic Affairs + Samples: -1: Savings include 咋 ^ ¥ &

-72-The size of this paper is suitable; Π Chinese National Standard (CNS) A4 is now available (210X297 mm) 503237 A7 B7 V. Description of the invention (Η) Table 1 (continued) No. XY m R M65 o! II 1-166 --Θα o-Me ^ ho 1 H M67 J 0 m- -N 1 -CIPh 0 3 H ~ M68 MeO〆0 rrhN ie〇k 0 1 H 1-169 Me, HO ^ U -N mountain e 0 1 H 1 -170 Xj MeO N -N, N people 0 i H 1-171 0 -N 0 2 H -73- (Please read the precautions on the back before filling this page) The paper size of the paper is applicable to China® house standard rate (CNS ) A4 is now available (2 丨 0X297 mm) 503237 A7 B7 V. Description of invention (W) Table 1 (continued) Printed by the Consumers' Cooperative of the Central Bureau of Samples of the Ministry of Economic Affairs «.

The size of this paper is applicable to China's "Home furniture (CNS > A4 present grid (2 丨 OX297 mm) 503237 ¾ Jilang Zhongmeng Mongolian horseman x-consumption combination it printed A7 B7 V. Description of invention (V) 1 (continued) > ft ^ b Edit XY m R 1-179 Ph Renren N Ren 1 Me o! U 1-180 jf) 7l 1 Me 0 3 H 1-181 tBu -N HO— ^ S 入 N Human IJi Human ^) ~ ^ Me tBu 0 1 H 1-182 I Me 0 1 H 1-183 -N iPK) Ren Ren N々_ 1 Me 0 1 H 1-184 MeO χ. 1 Me 0 1 H 1- 185 1 Me 0 1 H -75-(Please read the notes on the back before filling in this page) The size of the paper used in this edition is China® House Standard (CNS) Λ4 grid (210X 297 mm) 503237 A7 B7 V. Invention Explanation (W) Table I (continued) Printed by Shellfish Consumer Cooperatives, Central Bureau of Standards, Ministry of Economic Affairs

-76 · (Please read the notes on the back before filling this page) This paper size is applicable to China National Standard (CNS) A4 (2 丨 0X297 mm) 503237 A7 B7 V. Description of the invention (W) Table 1 ( Continued)

(Please read the precautions on the back before filling out this page) -77- 503237 A7 _B7_ V. Description of Invention Uif) Table 1 (continued) Printed by the Central Sample Horseman X Consumer Union of the Ministry of Economic Affairs «.

(Please read the precautions on the back before filling this page) • Stupid. The paper size of the book is applicable to the China® house standard rate (CNS > Λ4 is now (210X297 mm) 503237 A7 B7 V. Description of the invention (Μ) Table 1 (Continued)

X

Y m

R 1-206

BuCONH ----- n Βυ \\ 1-207 Η / ί)

Η 1-208 ΒζΟ

Η (Please read the precautions on the back before filling this page) Λ 衣 09 -2

Η 2 Η Order ο -2

Ν—Η ΟΗ 2 Η -2 Jiangyin, a kind of consumption cooperation between Jiangbei and Mabei in the economic state *.

νιπμμ ^

h NIP

OF 2 Η

The paper size of the table is applicable to China® Home Standard (CNS) A4 specification (210X 297 cm) 503237 A7 B7 V. Description of the invention (m Table 1 (continued) η

1-215 1-216 1-217 1-218

X ml

R

Ν J N \ sBuI Bz

tBuNH

-NA A Λ tBuNH Ν N " I

Pr ο 2 (Please read the notes on the back before filling this page), install ‘0

H

H order

—N

Me Ο

H 印 Printed by the Consumer Cooperatives of the Central Bureau of Standards, Ministry of Economic Affairs

Me

-N, Ν-I Me 1-219

Me

、 Ν mClPh 〇 Η This paper size is applicable to China National Standard (CNS) Λ4 specification (2 丨 0X297 mm) -80_ 503237 A7 _B7 V. Description of invention (V) Table 1 (Performance)

(Please read the notes on the back before filling this page)

—0-Refill A with one item-The size of the paper is applicable to China's furniture ratio (CNSM4 specification (2 丨 0X297mm) 503237 A7 B7 V. Description of the invention (^) Table 2 Employee consumption of the Central Procurement Bureau of the Ministry of Economic Affairs Co-operative seal ¾ No. X Υ m R 2-1 CU 1 0 2 H 2-2 丨 1 丨 0-2 H 2-3 r ^ / CPh3 1 ϋ 2 H 2-4 0 2 H 2-5 0 1 H 2-6 FREE β 0 1 H 2-7 FREE β 0 2 H 2-8 Co. & 0 IH This paper size is applicable to China's "Furniture Ratio (CNS) Λ4 Appearance (210 X297 mm) > 82 ~ (Please Read the notes on the back before filling in this page.)-Clothes · Order 503237 A7 B7 V. Description of the invention (τ〇 Printed by the Consumer Cooperatives of the Central Sample Bureau of the Ministry of Economy ¾ Table 2 (Continued) No. XY m R 2-9 Cc / 〇 .1 11 2-10 0 1 Η 2-11 W FREE β 0 5 Me 2-12 / iPr S 1 Η 2-13 丨 'Me 0 2 MeO 2-14 υψ Me 0 1 Η 2-15 η ° υ ^ ί / Et 0 1 Η 3 8 (Please read the notes on the back before filling in this page): Ε_ The size of the paper is applicable to the Chinese national standard (CNS) Λ4 now (2 丨 0X297 mm) 503237 A7 B7 5 2. Description of invention (Μ) Table 2 (continued) Printed by the company ¾ No. XY in R 2-16 Πυ〇 ^^ / Ogi 1 Me Ο 1 II 2-17 Me Me Me s 4 Cl 2-18 __ / 0 3 OH 2-19 s 2 Bu 2-20 Xv 0 5 H 2-21 H0 ^ \ / iBu 0 1 H 2-22 ΧλΛ 0 1 H This paper size applies to China National Standard (CNS) Λ4 specification (2 丨 0X297 mm) -84- (Please read the back (Please fill in this page again)

, 1T 503237

Keijiro loses 4 | Matches 11 Shao Fei combined f ±. ¥ it V. Description of the invention (^) Table 2 (continued) Number XY m R 2-23 1 Me o 1 It 2-24 people 1 Me 0 1 H 2-25 1 Me 0 i H 2-26 ΒΓνυ ^ ί I Me 0 1 H 2-27 T ii 1 Et 0 l H 2 «28 1 Me 0 1 H 2-29 h2n ^. 1 Me 0 l H -85_ (Please read the precautions on the back before filling this page) This paper applies Chinese National Standards (CNS) Λ4 Appearance (2 丨 0X297 mm) 503237 A7 B7 V. Description of Invention (4) Table 2 ( Jing) Printed by the Shellfish Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs *-No. X Υ ιπ R 2-30 AcHN, ^ s XXx Me ο t II 2-31 ο 1 Η 2-32 Me2N ^^ \ χλΛ 0 ι Η 2-33 Η * Bu— 丨 Χ × \ 0 1 Η 2-34 Me ΧλΛ 0 1 Η 2-35 Η Ph— 山 ΧλΛ 0 1 Η -86- (Please read the precautions on the back before filling this page) This paper In the standard application, "National Standard (CNS > A4 is now available (2 丨 0X 297 public health) 503237 Α7 Β7 V. Description of the invention () Printed by the Consumer Cooperatives of the Central Procurement Bureau of the Ministry of Economic Affairs. 2-36 AcNH ^ \ s 2 Me 2-37 ι 0 4 MeO 2-38 L 0 1 H 2-39, OMe 1 tBu 0 1 H 2-40 L 0 1 H 2-41 jOl fire c 丨 people 乂 7 people Et 0 2 Ci 2-42 jOl fire Me0 people ^ people Me 0 1 H The paper standard is common Chinese national standard (CNS > A4 specification ( 210 × 297 mm) -87 «(Please read the notes on the back before filling in this page)

503237 · Α7 Β7 V. Description of the invention (W) Table 2 (continued) Printed and edited by the Shell Specimen Consumer Cooperative of the Central Samples Bureau of the Ministry of Economic Affairs XY m R 2-4.1 Me〇- ^ A Me υ 4 II 2-44 0 i MeO s s 1 H 2-45 XU O 1 H 2-46 0 1 H 2-47 _ uy Bu 0 2 H 2-48 x〇s 1 Me 2-49 XX? L 0 4 Me -88 ~ (Please first (Read the notes on the back and fill out this page)

、 1T i # This paper is in accordance with China State Standard (CNS) Λ4, and it is 2 × 0X297 mm. 503237

AB V. Description of the invention (π) Table 2 (Performance) XY m R 2-50 _ k Ο! 11 2-51 Me ο I u 2-52 S -2 H 2-53 & Spr 0 2 Me 2 -54 έο S 3 H 2-55 _ Me 0 1 MeO -89- This paper size is suitable for China National Standard (CNS) A4 (210X297) (Please read the precautions on the back before filling this page) 503237 A7 B7 V. Description of the invention (and) Table 2 (continued) Printing number of the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs | XY ill R 2-56 sl H 2-57 Λ 1 0 2 H 2-58 1 0 4 Me 2 -59 CXx 0 1 H 2-60 〇Λ 0 2 H 2-61 勹 s 3 H 2-62 Λ rile 0 IH-90- ---- install ------ order ------- ( Please read the precautions on the back before filling out this page.) This paper is applicable to "W Jiabiaofeng (CNS) Λ4 grid (210X 297 mm) 503237

A

7 7 B V. Description of the invention () Printed by the Consumers' Cooperatives of the Central Bureau of Standards of the Ministry of Economy 2 (Continued) No. XY ηι R 2-63 _ person 0 2 (i 2-64 Λ 0 3 H 2-65 Λ s 1 H 2-66 〇Λ L 0 1 H 2-67 Cxx 0 2 MeO 2-68 ΟΛ 0 1 H 2-69 people 5 H -91-(Please read the precautions on the back before filling this page) The size of this paper is in accordance with China State Standard (CNS) A4 (210X297 mm) 503237 A7 B7 V. Description of the invention (^) \ »y Continued c 2Table 1 | Edit

X γ 0

R ο -7 2-

y ((2

ο Η 2 -7 2-

ο (Please read the notes on the back before filling this page) Pack-2 Η 73 2-

Ν 丨 C

S Η

1T 74 2-

Ν— f Ν ο 4 Η 2-Stamped by the Consumer Cooperatives of the Central Sample Bureau of the Ministry of Economic Affairs ¾ 76 I 2 2

ΝIΗ, ν Ν Ν—Η

ο Η ο ο The paper ^ scale selection in the guinea pigs (CNS) 8 4 grid (2ί〇 χ-2 young male *) 3 Η ϊ fr -92- 503237 A7 V. Description of the invention (G)

(Please read the precautions on the back before filling in this page) The paper size applies to the Chinese National Standard (CNS) Λ4 specification (2 丨 〇κ297 mm) 503237 Α7 Β7 V. Description of the invention (Suppression) Table 2 (Continued I)

X γ ml

R 2- 6 8 2- 2- 2-88 2-89 ο -9 2-

Ν e N—Et

Γ

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Ν Η Applicable to the standard of this paper "* 家 标 隼" ([Milk> 8; 4 present (2 丨 0 dogs 297 public health) 503237 A7 B7 V. Description of the invention (K) Table 2 (continued) Breaking down !: Save on fees including Hanshe

. (Please read the precautions on the back before filling this page) -95- This paper size uses the Chinese national rate (CNS > A4 now (2 丨 OX297 mm) 503237 A7 B7 V. Description of invention (") 2 (continued) ¾ Qilang Zhongya Puyangyang member 11 writes ^^ 卞 ijl.f gets number XY in R 2-102 η 1 1 Me 0 1 H 2-103 rr 1 1 Me 0 2 H 2-104 r , I 1 0 2 H 2-105 n 1 j 1 0 4 H 2-106 aNj 0 1 H 2-107 Me & 0 .2 H 2-108 Br 0 3 H 2-109 〇Λ s 1 H -96 -This paper size applies Chinese National Standard (CNS) Λ4 specification (210X297 mm) (Please read the precautions on the back before filling this page) Λ Clothing. 503237 AB * V. Description of the invention (ο) Table 2 (continued) No. XY m R 2-110 Γ ^ Ν ~~ ίΐ person OH 0 1 H 2-111 XXx 0 i H 2-112 C, Y ^ N—π 0 2 H 2-113 s 1 H 2-114 r ^ Nπ 0 1 H 2-115 Can N—Π 0 3 H 2-116 r ^ N—π People Me 0 1 H 2-117 Can N—1 People Me s 2 H 2-118 0 1 H -97- (Please first Read the notes on the reverse side and fill in this page) This paper size is applicable to China National Standards (CNS) Α4 specification (210 × 297 G 蠖) 503237 A7 B7 V. Description of the invention (M ) Table 2 (continued)

Squid XY m R 2-119 〇5 Me 2-120 Can N—π person Et 0 1 MeO (Please read the notes on the back before filling in this page) Binding-Order ~ 98 ~ Tongzhou Zhongjia Support Co., Ltd. (CNS) A4g (2 丨 0X297 mm) 503237 A7 B7 V. Description of the invention (strong) Table 3 Number XY m R 3-1 CO I 0 2 H 3-2 cu " Η 0 2 H 3-3 Eight CPh. W 1 0 2 H 3-4 w Me 0 2 H 3-5 0 1 H 3-6 ULA 0 IH 3-7 0 2 H 3-8 ULA k 0 1 H This paper size is applicable to the Chinese standard (CNS) ) A4At (2 丨 〇 × 297mm) (Please read the precautions on the back before filling this page):

, 1T -99- 503237

A Table 3 (Jing) Employees 'Cooperatives' Seal of the Central Sample Bureau of the Ministry of Economic Affairs No. X Y m R 3-9 o 3 McU 3-10 XXX. 0 1 H 3-11 W 0 5 Me 3-12 ks 1 H 3-13 V / Me 0 2 MeO 3-14 Me0 \ ^ \ / Me 0 1 H 3-15 HOr) ^ Me Me 0 l H- 100 ~ (Please read the precautions on the back before filling this page)

、 1T This paper size applies to Chinese National Standards (CNS) Λ4Λ grid (210X297 mm) 503237 A7 B7 V. Description of the invention () Table 3 (continued) Compounds are compiled XY m R j-16 W 1 Me 〇 1 H 3 -17 Me Me Me s 4 Cl 3-18 rw MeA ^ S Me 0 3 OH 3-19 c, xy Me s 2 Bu 3-20 〔1 1 H 0 5 H 3-21 TO | iBu 0 1 H 3- 22 0 1 H Table paper size is applicable to China National Standard (CNS) A4 specification (210X297 engraving) -10 (please read the notes on the back before filling this page) 503237 A7 B7 V. Description of Invention (P) Ministry of Economic Affairs Medium sample X. Μ f% it Table 3 (jing) Number X Υ m R 3-23 & 0 1 H 3-24 H〇XXx 0 i H 3-25 XXx 0 1 H 3-26 s 1 H 3-27 〇2ΝΌζ \ 0 1 H 3-28 0 l H 3-29 XX \ 0 1 H -102-Please read the notes on the back δ and fill in the% Rate (CNS) Α4 (210x297 mm) 503237

A B7 V. Description of the invention (w) Table 3 (continued) X Υ m R 3-30 AcNH, ^ \ ΧλΛ 0 1 Η 3-31 k ο 1 Η 3-32 MeNHY ^ \ 0 1 Η 3-33 Χ ΧΧΛMe 0 1 Η 3-34 Me Bz ~ Ny ^ \ person ο 1 Η 3-35 Me Ph- Όζ \ 0 1 Η (Please read the precautions on the back before filling this page).

、 1T -103- This paper size is applicable to Chinese National Standard (CNS) M specifications (2 丨 〇 < 297 public broadcasting) 503237 A7 B7 V. Description of the invention (94) Table 3 (continued) Ed. 3-36 3 -37

X

Y ηι

R

Me

N I H

O

MeO (Please read the notes on the back before filling out this page)

This paper size is applicable to China National Standard (CNS) A4 (2 丨 0X297mm) 503237

B V. Description of the invention (^) Table 3 (Dragon) Edit XY m R 3-43 Me〇AAA Me 0 4 H 3-44 Human MeO s s IH 3-45 χ〇i 0 1 H 3-46 W 0 1 H 3-47 tBu 0 2 H 3-48 x〇ks 1 Me 3-49 Xp 0 4 Me -105-(Please read the notes on the back before filling out this page)-Binding 'The size of the paper is suitable for China Standard rate (CNS) A4 is now available (210X 297 male) 503237 A7 B7 V. Description of invention (%) Table 3 (continued) For XY m R 3-50 o I 11 3-51 1 j Y Me 0 1 Fi 3-52 1 jY Me 0 2 H 3-53! Ργ 0 2 Me 3-54 Bu s 3 H 3-55 0φ Me 0 1 MeO -106- (Please read the notes on the back before filling in this page) Binding-Book size 遢 Λ 《«Home Slope (CNS > A4 size (2! 〇X297mm) 503237 A7 B7 V. Description of the invention (W) Table 3 (continued) X Υ m R 3-56 s 1 II 3-57 1 0 2 H 3-58 Me0-y ^ X 1 0 4 Me 3-59 Λ i 0 1 H 3-60 〇h 0 2 H 3-61 Ox bs 3 H 3-62 Λ 0 1 H -10?-(Please read the precautions on the back before filling this page)

、 1T The standard of this paper is applicable to Chinese National Standard (CNS) A4 (210 X297 mm) 503237 A7 B7 V. Description of the invention (pair) m R 3-63 〇Λ ώβ υ 2 11 3-64 U! Me \ 0 3 H 3-65 u, 〆i Me \ s 1 H 3-66 Et 0 1 H 3-67 0 2 MeO 3-68 L · 0 1 H 3-69 0 s 5 H -108 · ~ (Please read the precautions on the back before filling in this page) This paper size is applicable to China National Standard (CNS) Α4 now (2 丨 0X297 mm) 503237

7 7 AB V. Description of the invention () Table 3 (continued) Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs ^^ 0 No. XY m R 3-70 People 0 1 Cl 3-71 Ιργ ο 1 H 3-72 1 0 2 H 3-73 1 s 3 H 3-74 〇1 1 0 4 H 3-75 Cu ^ b 0 1 H 3-76 〇 / 0 3 H 3-77 / ζχχ 1 Me 0 1 H This paper size is applicable China National Standard (CNS) A4 Specification (210X297mm) -109-I Binding (Please read the precautions on the back before filling this page) 503237

A B Explaining the fifth statement c3

0 This paper size is applicable to China W House Standard (CNS) A4 now < 210X297 mm) -------- Installation— (Please read the precautions on the back before filling this page)

, 1T 503237 A7 B7 ......... II 丨 · '1 TgfllMiii .......... ........................................ ........... _ 丨 丨 ι ................ ιι_ V. Description of the Invention (ICM) Table 3 (Continued)

(Please read the notes on the back before filling this page)

、 1T The standard of this paper is applicable to China National Standard (CNS) A4 specification (2 丨 OX 297 mm) 503237

3-97-Pr H cx • > r

3-98 3-99

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Edit XY m R 3-102 r T 1 I Me o IH 3-103 rr 1, N 、 1 Me '0 2 H 3-104, j 1 0 2 H 3-105 n 1 j 1 0 4 H 3 -106 r ^ N—π 0 1 H 3-107 Me r ^ Nπ \ 0 2 H 3-108 ΒΓγ ^ N__ person Br 0 3 H 3-109 s 1 H ------------ --IT ------ 0 (Please read the precautions on the back before filling out this page) -113- This paper size is applicable to the standard of domestic standard (CNS) A4 (2IOX297)

7 7 A B

5-1 10 3-111 3-11: 3-113 3-114 3-115 M16 3-117 Description of the invention (w) Table 3 (Continued number M! 8

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Cl

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N N-

I N-

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(Please read the precautions on the back before filling out this page.) Installation, 11 -115-This paper's standard is applicable to the Chinese national standard "CNS" Λ4 is present (2 丨 0X 297 mm) 503237

A

7 B Economy Lang licking wheat Goubei 11 Inferior f containing 阼 <11 ¥ pack V. Description of invention (4) Table 4

XY m R 4-! 1 o 2 Π 4-2 CX / 1 Π 0 2 H 4-3 Eight CPh fly / 1 1 1 0 2 H 4-4 Me 0 2 H 4-5 ζχλ A 0 1 H 4-6 / 1 1 0 1 H 4-7 [f | 1 0 2 H 4-8 _ k 0 i H (Please read the notes on the back before filling out this page)-Binding-Ordering paper size for China Standard rate (CNS) A4 specification (2! OX297 mm) -116- 503237 A7 B7 V. Description of invention (W) Table 4 (continued) Printed by the Bayer Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs «.

XY m R 4-9 1 3-PhPr u J II 4-10 ________ / ClNjC, o 1 H 4-1 1 0 5 丨 Me 4-12 0 s 1 H 4-13 CtX 0 2 MeO 4-14 Me0 \ ^ \ / 0 IH 4-15 Me 0 1 II -117- (Please read the precautions on the back before filling this page) Binding-The size of the paper is applicable to China National Slope (CNS) 8 and 4 (2! 〇 × 297 mm) 503237 A7 B7 V. Description of the invention) Table 4 (continued) L ·. Number XY m R 4-16 1 Me 0 1 U 4-17 Me ΐ- / VS Me Me s 4 Cl 4-18 / L 0 3 OH 4-19 β, ι ^ ί 〆s 2 Bu 4-20 ^ 1 1 0 5 H 4-21 L 0 l H 4-22 / 1 1 1 Me 0 i H -118- iiL scale Applicable "National Standards (CNS) Λ4 now (21〇X 297 mm) (Please read the precautions on the back before filling out this page). Installation ·-一 α 503237 A7 _B7 Five 'Invention Description (W) Table 4 ( Continued) Number XY m R 4-23 1 1 1 Me o! H 4-24 HOn i 1 Me 0 1 H 4-25 Me〇Y ^ Person 0 i H 4-26 1 Me 0 1 H 4-27 χλλ 0 ! H 4-28 Me \ r ^ r \ person 1 Me 0 1 H 4-29 T ii rile ol H -119- (Please read the precautions on the back before filling this page) Binding this paper size Shizhou "« Home Furnishing (CNS) 4 now grid "210X297 mm) 503237 A7 B7 V. invention is described in (u.) Table 4 (Continued)

-120- (Please read the precautions on the back before filling this page) Packing, 1T This paper size is suitable for China National Standard (CNS) A4 (210x 297 public seam 503237 A7 B7) V. Description of the invention l · ', ) Table 4 (continued) Number XY m R 4-36 Λ〇Νί ^ \ \ 丨 1 s 2 Me 4-37 r ULA 1 fhi o 4 MeO 4-38 Ci Λ-π 1 1 0 l H 4-39, 0Me 0 l H 4-40 〔II 0 1 H 4-41 0 2 CI 4-42 _ 0 1 H -121- This paper size is applicable to the Chinese National Standard (CNS) A4 (2 丨 〇 × 297 mm) (Please read the precautions on the back before filling this page) Equipment · TJ- In II · -5 503237 A7 B7 V. Description of the invention (^) Table 4 (continued)

-122- (Please read the precautions on the back before filling out this page) Packing--5 The paper size is applicable to the Chinese cabinet ladder standard ((1 ^) 8 4 standard (210/297 public waste &gt; 503237 A7 _B7 5) & Explanation of the invention (&quot; ^) Table 4 (jing) No. XY 111 R 4-50 _ o I ii 4-51 W 0!, R 4-52 _ 1 Me 0 2 H 4-53 / 1 1! Pr 0 2 Me 4-54 W fL s 3 H 4-55 / 1 1 Me 0 1 McO -123- (Please read the notes on the back before filling out this page) Binding and binding &lt; CNS) Λ4 specification (2 丨 OX297 mm) 503237 A7 B7 V. Description of the invention (ι4- Table 4 (continued) No. XY m R 4-56 1 Bz s 2 H 4-57 _ ”N '' 1 0 2 H 4-58 1 0 4 Me 4-59 Λ person 1 H 0 IH 4-60 _ person! H 0 2 H 4-61 _ s 3 H 4-62 勹 rile 0 1 ll (Please read the back (Please fill in this page for attention)

、 1T -124- This paper is suitable for the standard / fl China National Standard (.CNS) Λ4 is present (2i0x297 mm) 503237 A7

__ W 5. Description of the invention (&quot; &lt;) Table 4 (Performance) Editor XY m R 4-63 〇2 Π 4-64 〇 person 0 3 Η 4-65 _ person S 1 Bu 4-66 Et 0 1 Η 4-67 _ 0 2 MeO 4-68 έυ 0 1 Η 4-69 _ Mountain e S 5 Η -125- (Please read the precautions on the back before filling out this page), *! * This paper size is suitable for China China National standard (CNS) A4 now (2 丨 0X297 mm) 503237 A7 B7

(Please read the precautions on the back before filling this page) 503237 V. Description of the invention (π) A7 B7 128 Table 4 (continued) No. 4-78 4-79 4-80 4-81 4-82 4-83 4 -84

X

Y ΓΠ

R

Me Η

Me

Cl Η Η Εί Η (Please read the notes on the back before filling out this page) Binding and binding paper size Tongzhou "« Furniture Ratio (CNS) Λ4 now (21〇X 297 mm) -127- 503237 A7 B7 V. Description of Invention (^) Table 4 (Continued)

-128- (Please read the precautions on the back before filling this page). The size of this paper is applicable to the Chinese national standard (CNS &gt; A4 now (210x 297 mm) 503237 A7 B7 5. Description of the invention () Table 4 (Continued)

(Please read the notes on the back before filling in this page) Qin. 丨 MI-129- This paper size is applicable to China's "House Standard Card (CNS &gt; Λ4) (2 丨 〇X 297 mm) 503237 ¾ Bennian ^ Member ΙΙΛιδτ ^ Take fJL.fx ^ A7 B7 V. Description of the invention (…) Table 4 (continued) Number XY m R 4-102 〇1, N〆1 Me \ 0 1 H 4-103 1 0 2 H 4-104 η 1-N 1 0 2 H 4-105 ri -N 1 s 4 H 4-106 ——r 0 1 H 4-107 UNJ \ 0 2 H 4-108 ΒΓγ ^ N—π Br 0 3 H 4-109 cu sl H -130- (Please read the precautions on the back before filling out this page) Packing · -1 mouth This paper size is the standard of the Chinese circle of China (CNS) A4 Grid (2 丨 〇 × 2 &lt; Π 公) 503237 A7 B7 V. Description of the invention () Table 4 (Fine) Editing squid X Υ m R 4-110 Π Ο Η 0 1 Η 4-111 C1, Guang N—Π 0 1 Η 4-112 Xu 0 2 Η 4-113 Cl, In N—π \ S 1 Η 4-114 ——r 0 1 Η 4-115 Xu 0 3 Η 4-116, Me 0 1 Η 4-117 / Me r ^ N— ~, S 2 Η 4-118 0 1 Η The paper size in Tongzhou * «Furniture Ratio (CNS) A4 Specification (2 丨 0X297mm) &lt; 131- (Please read the notes on the back before filling This page) equipment - 503 237 Order

7 7 A B V. Description of the invention () Table 4 (· continued)

-------- •. 衮 ------, 玎 ------- (Please read the precautions on the back before filling out this page) -132- This paper standard is generally Chinese national standard 隼(CNS) A4 wash case &lt; 2 丨 O x 297 mm) 503237 A7 B7 V. Description of the invention (H) Table 5

(Please read the precautions on the back before filling in this page) Binding · Binding-133 · This paper size is universal China® Home Slope (CNS) A4 Washing Grid (2 丨 0X297 Public Celebration) 503237 A7 B7 II ιιιιιιιιιιιι ι ... .......- 111111111 111111 --------------- 111111111 surface 1111111 ------------ -· 25. Description of the invention) Table 5 (Jing) Printed by the Shellfish Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs

Editing delay XY m R 5-9 0 3 H 5-10 XXX 0 1 H 5-11 Η〇γ ^ \ / 0 5 Me 5-12 CX / U s 1 H 5-13 〔II, ^ a a 0 0 MeO 5-14 Me〇Y ^ / Me 0 1 H 5-15 jC Mc Me 0 i H -134- (Please read the precautions on the back before filling this page) 士 ----- 111I-== 11 = 11 -................................— 1 «_l'll1, ... '· ιι-TJ i .. ...........- nn ml i In * Free · ν Swallow This paper size applies to China National Standards (CNS) Μ Presentation (2 丨 οκ 297 public interest) 503237

In this paper's standard 遢 / fl, "Jia Jiafeng (CNS) 8 4 grid (2 丨 0X297 mm) 503237 A7 B7 V. Description of the invention (^) Table 5 (continued) Editing squid XY in R 5-23 1 1 Me 0 1 H 5-24 1 Me 0 1 H 5-25 Μ6〇γ ^ Human I Me 0 1 H 5-26 1 Me 0 1 H 5-27 1 Et 0 1 H 5-28 χΛΛ 1 Me 0 1 H 5-29 1 Me 0 l H -136- ---------- (Please read the notes on the back before filling out this page) Α4 is present (2 丨 〇 × 297 mm) 503237 A7 B7 V. Description of the invention () Table 5 (continued) Compilation system XY m R 5-30 Bz 1 AcN \ ^ X person 1 Me 0 IH 5-31 ^ ν &quot; Πλ k 0 IH 5-32 Prri \ 1 Me 0 1 H 5-33 Η Βυ_Νγ ^ χ 1 Me 0 1 H 5-34 Me Βζ-Νγ ^ \ I Me 0 1 H 5-35 H Ph-N 'Ya 'Person 1 Me 0 1 H 137- i (Please read the precautions on the back of the eye before filling this page) Order 503237

AB Central Central Mabei Workers Consumer Cooperative Co., Ltd. ¥ Included 5. Description of the invention (^) Table 5 (Performance) XY m R 5-36 AcN% ^ XXx s 2 Me 5-37 L 0 4 MeO 5-38 Cl 6cx w 0 1 H 5-39 / 0Me CXa Me 0 1 H 5-40 〔II 0 1 H 5-41 XXFire Et 0 2 Cl 5-42 j〇i Me0 ΐ 人 Me 0 l H -138- (Please read the precautions on the back before filling this page) 1:-The paper size is applicable to the furniture ratio (CNS &gt; Λ4 wash case (2 丨 0X: W)) 503237 A7 B7 V. Description of the invention Table 5 ( Continued) Knitting XY ill R 5-43 0 4 H 5-44 〇1 Human MeO Η s 1 H 5-45 XY A 0 1 H 5-46 0 1 H 5-47 0 2 H 5-48 s 1 Me 5-49 Me 0 4 Me This paper is a Chinese standard Wuzhou standard house (CNS) A4 (210X297 mm) -139- (Please read the precautions on the back before filling this page) 503237

Me The paper size is in accordance with China National Standard (CNS) A4 (210X297 mm) —140-

503237 A7 B7 V. Description of the invention (…)) 碛 C 5 Form i Printed by the Shellfish Consumer Cooperative of the Central Sample Bureau of the Ministry of Economic Affairs

(Please read the notes on the back before filling in this page) -C0 The paper size is applicable to Chinese interpreter standards (CNS) A4At grid (2 丨 OX297 mm) 503237 A7 B7 V. Description of the invention (eg) Table 5 (Performance ) Kane X Υ m R 5-63 〇Λ 0 2 Η 5-64 0 3 Η 5-65 Λ S 1 Η 5-66 勹 —λ 0 1 Η 5-67 _ person ir 0 2 MeO 5-68 i ^ s_ 0 1 Η 5-69 f ^ N_ S 5 Η -142- The paper size is suitable for the national standard of China (CNS &gt; A4 this grid (2 丨 〇 ^ 297 eaves) (Please read the precautions on the back first) (Fill in this page again.) Packing 、 · ιτ 503237 Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 V. Description of the invention () Table 5 (continued)

5 -7 5 76-5 (Please read the notes on the back before filling this page)

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Ν \ eΝΙΜ ο

H Η Η This paper size applies to China National Standard (CNS) Α4 size (210X297 mm) -143- 503237

A λ / fl \ Explicitly explain 5) Continued C 6

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The standard of this paper is applicable to Chinese standard (CNS &gt; 8 4 grids (2 丨 OX 297 mm) -145- 503237 ΛΊ

Ml V. Description of the invention (4) Table 5 (continued)

(Please read the precautions on the back before filling this page) &gt; .Installation, v5 • 146-This paper's standard is applicable to China National Standard (CNS) A4 (2 丨 () X2W public eaves) 503237 A7 B7 V.发明 发明 （⑻） Table 5 (continued)

X

Y m

R 5-102

Ο Η 5-103 5-104 5-105 5-106 5-107

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(Please read the precautions on the back before filling this page) BOOK-148 · This paper size is applicable to Chinese National Standard (CNS) Λ4 is present (2 丨 OX 297 mm) 503237 Printed by the Shell Sample Consumer Cooperative of the Central Sample Rate Bureau of the Ministry of Economic Affairs ¾ A7 B7 V. Description of the invention (^) Table 5 (continued)

-149- (Please read the notes on the back before filling this page) 1-

* 1T This paper is in accordance with China National Standard (CNS) A4 (2 丨 0X297 mm). The Central Bureau of Standards, Ministry of Economic Affairs, Shellfish Consumption Cooperation, Du Yin ¾ 503237 A7 B7 V. Description of the invention) Is the following, which is the compound N 0.1-1, Bu 2, Bu 3,1-6, 1-57, 1-59, 1-62, 1-72, 1-81, 1-91, 1-93, 1 -106, 1-121, 1-122, 1-125, 1-130, 1-134, 1-135, 1-137, 1-140, 1-142, BU 153, BU 156, BU 158, 1- 161, 1-177,1-179, 1-180, 1-1 82, 1-1 83, 1 -207 and 1-218, of which the compound ^ No. 1-1, 1-57, 1-62, 1-91, 1-93, 1-106, 1-122, 1-125, 1-130, 1-134, 1-137, Bu 140, 1-142, 1-153, 1-156, 1-1 7 7, 1-179, BU 180, BU 182, BU 183, 1-207 and 1-218 are more preferred. Still more preferred compounds are compounds N ο · 1-6 2, 1-9 3, 1-1 2 5, Bu 1 3 4, 1-140, 1-1 42, 1-153, 1-177, 1-179 , 1-182, 1-183 ¾ 1 — 207 〇 The best compound is compound N 〇: 1-9 3 5- (4- (3-methyloxazolo [5,4-b] pyrimidine-2- Methoxy) benzyl) triazolidine-2,4-dimeric; 1-125 5- {4- (5-chloro-3-methyloxazo [5, 4-b] pyridine-2- Methoxy) benzyl} pyrazolidine-2,4-difluorene | 1-142 5- {4- (5-methoxy-3-methyloxazo [5, 4-b] pyridine- 2-methylmethylamino) benzyl} carbazolidine-2,4-dihedral 1-153 5- (4- (5-hydroxy-3-methyloxazolo [5, 4-b] pyridine-2 -Ylmethylamino) benzyl} oxazosin-2,4 -diphenyl; 1-182 5- {4- (5 -ethoxy-3-methyloxazolo [5, 4-b] Pyridin-2-ylmethylamino) benzyl) pyrazolidine-2,4-dione; 1-183 5- {4- (5-isopropoxy-3-methyloxazolo [5,4 -b] pyridin-2-ylmethylamino) benzyl} pyrazolidine-2,4-di_. -150- This paper size applies to China National Standard (CNS) A4 (210X297 mm) ----------_ · 策 ------ 1T, ------ # (Please (Please read the notes on the back before filling out this page) 503237

A

7 B Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of Invention () The physical properties of some of the compounds in Tables 1 and 2 are shown in Table 3. Table 3 Compound No, melting point (° C) Compound No. melting point (° 〇) 1-59 55.8-58.2 1-130 212-214 1-62 46.1-48.9 1-158 244-246 1-57 132.8-135.6 1- 134 211-213 1-2 42.6-44.5 1-135 189-191 1-3 66.6-70.0 1-137 204-205 1-1 42.3-44.6 1-140 203-205 1-93 223-225 1-156 264 -265 1-72 200.0-202.4 1-81 183-185 1-106 197-202 1-161 88-91 1-6 174.3-175.5 1-177 166-168 1-107 205.9-207.0 1-207 210-211 1-121 210-212 1-153 240-242 1-122 231-232 1-182 245-246 1-123 185-186 1-183 210-212 1-91 247-248 1-190 96-100 1- 124 205-207 1-179 211-213 1-125 222-223 1-142 258-260 1-218 226-228 1-142 Hydrochloride 255-262 1-218 Trifluoroacetate 229-230 1-142 Fumarate 245-253 -151- (Please read the notes on the back before filling in this page) This paper size applies to Chinese National Standard (CNS) A4 specification (210X297 mm) 503237 A 7 B7 V. Description of the invention () Bovine living compounds of formula (II) and their salts have lower blood glucose concentration, slow obesity, and alleviate impaired glucose tolerance , Suppress of hepatic regeneration, reducing blood lipid levels and the inhibitory activity of aldose reductase IS. Therefore it can be used for the prevention and / or treatment of hyperglycemia, obesity, hyperlipidemia, diabetic complications (including retinopathy, nephropathy, neuropathy, cataracts, coronary artery disease and arteriosclerosis) and also for obesity related Hypertension and osteoporosis. Compound (I I) can be administered in a variety of forms well known in the art, depending on the disease to be treated and the age, condition and weight of the patient. For example, it can be formulated as a drug H, capsule, granule, powder, or syrup for oral administration of a compound; or it can be formulated as an injection (intravenous, intramuscular or subcutaneous) for parenteral administration, and diffusely dripped. Or suppository. In terms of ocular mucosal pathway, it can be formulated as eye drops or eye drops. These formulas can be printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) in a unified way. A If desired, the active ingredients can be combined with any traditional additives, such as excipients. , Binding agent, disintegrating agent, lubricant, flavoring agent, rib solvent, suspended rib agent, emulsifier or coating agent. Although the dosage depends on the patient's symptoms, age and weight, the nature and severity of the disease to be treated or prevented, the route of administration and the type of drug, but the recommended daily dosage for adults is generally 0.01 to 20 GQ mg And it can be administered in a single dose or in divided doses. The activity of the compound (I I) is illustrated by the following test. -152- This paper size is in accordance with Chinese National Standard (CNS) A4 (210X297 mm) 503237 A7 B7 V. Description of the invention () Test 1 Long rfn enamel 袢 Use KK hyperglycemic male rats each with a weight of at least 40 grams As a test animal. The test compound was mixed with a 1: 1 mixture of polyethylene glycol 400 and water. Each animal was orally administered with the test compound in the amount shown in Table 6 below, and thereafter fed freely for 18 hours. At the end of this time, blood was collected from the tail vein without anesthesia. The blood glucose concentration (BGL) was measured with a glucose analyzer (GL-101, manufactured by Mikasa Kasei Corporation or Glucoroder.F, manufactured by Shino Test Co., Ltd.). Hypoglycemic power is calculated by the following formula: Hypoglycemic power (%) = [BGLS -BGLt) / BGLS] X100 where: BGL s is the blood glucose concentration in the solvent-only group but no active compound group; and BGLt is the administration test Blood glucose concentration in a compound group. The results are shown in Table 4 below, where each compound (I I) is identified by the number of the example prepared as described below. Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the notes on the back before filling this page) -153- This paper size applies to China National Standard (CNS) A4 (210X297 mm) 503237 A7 _B7 V. Description of the invention (, ☆) Table 4 Example N of the compound printed by the Consumer Cooperative of the Central Government Bureau of the Ministry of Economic Affairs. Dose (mg / kg) Hypoglycemic effect (%) 1 ~ 59 10 13.2 1-62 1 2 7.7 1-57 10 2 7.0 1-3 10 16.2 1 ~ 1 10 2 0.9 1-93 1 2 4.7 1-106 10 2 7.6 Bu 6 1 11.6 1-122 1 3 4.0 Bu 91 1 13.8 1-125 1 37.1 1-134 1 2 4.5 1-137 1 10.2 BU 140 1 2 1.7 As shown in Table 4, compound (II) exhibited excellent activity. Test 2 抑制 Inhibitory effect of savage deer brew ^ S.Hymani〇JH Kinoshita [J.Biol.Chem., 240, -154- Winter paper size is applicable to China National Standards (CNS) Λ4 present grid (2 丨 ox 297 (Mm) (Please read the notes on the back before filling this page) ♦ 503237 A7 B7 V. Description of the invention (like) 8 7 7 (1 9 6 5)) f0 K.Inagaki, I. MiwafO J.Okuda [Arch Biochero · Biophys ·, 316,377 (1 982) 1 Formula 1 is used to isolate and partially purify bovine lens aldose reductase, and its activity is determined by Varma et al. [B i 〇chem. P har ni ac., 2 5 (2 5 0 5 (197 6)) optically -1 determination 〇 Measure the inhibitory effect of compound (II) at 5 # g / m [concentration of enzyme activity, and this measurement value is used to calculate the IC value. The results are shown in Table 5 below. Table 5 Inhibition of compounds in 5 / ig / ml I C50. Example N ο · Inhibition (%) (mg / inl) (Please read the precautions on the back before filling this page) Employees in the Ministry of Economic Affairs Consumption inclusive ¾ 1-59 54.5-1-62 58,1 3.2 1-57 noodles 3.7 1-2-2.3 1-1 47-1-93-1.0 1-106 53.3-Bu 121-1.7 1-122 -2.6 1-123 53.9-1-91-2.4 1-124 59.1 2 .Ί 1-125-1.8 1-130 76.3 0.8Θ 1-134 61.6 1.8 1-137 77.2 1.8 1-140 94.9 1.3 1-156 Θ1. 6 0.89 1-161 91.8 0.85 -155- The size of this paper is suitable / fl Chinese National Standard (CNS) Λ4 Yuege (210X 297 mm) 503237 A7 B7 V. Description of the invention () Test 3 Toxicity of toxic compound (II) Tested in 5 groups of F34 4 male mice. The test compound was administered orally to each test animal at a dose of 50 mg / kg body weight / day for 2 weeks. The test compounds used were Nos. 9 and 1-12. The animals were observed continuously for 2 weeks, and during this period, they did not show abnormalities due to the test compound. In view of the actual dose administered to each animal, its zero lethality shows that compound (II) has very low toxicity. The invention is illustrated by the following non-limiting examples. In these examples, the preparation of some final substances in these examples is illustrated by the subsequent preparation examples. Example 1, 5- "4- (2-Ethyl argon, methyl argon, and even benzyl) benzine 1 favor_pyridine-2.4-Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (Please read the precautions on the back before filling in this Page) 100 g of 4- (2-bromo-2-butyrocarboxyethyl) benzeneaminoacetic acid methyl ester (prepared as described in Preparation Example 3) and 22 g of sulfur P in 200 ml of ethanol solution are heated under reflux 2 · 5 hours. Thereafter, a 2 N aqueous hydrochloric acid solution was added and heated under reflux for 5 hours. At the end of this time, the solvent was distilled off under reduced pressure, the residue was diluted with water and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, The solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography using a 2: 5 volume ratio of ethyl acetate and hexane as an eluent to obtain 19.4 g of the title compound in 105. -1 0 6 ° C melting. -15 6- This paper size applies Chinese National Standard (CNS) A4 (210 X 297 mm) 503237 A 7 B7 V. Description of the invention () Example 2 R- "4- (2.2 -Di 7, MZ.ffi even) Ye very much favor _pyridine-2.4-di_ Under ice cooling, 5 3 Q mg of 5-(4-hydroxybenzyl) ffazolidine-2,4-dione Add to 260 mg of hydrogenated pin (a 55% by weight dispersion in mineral oil and washed with toluene in advance) in 5 ml of dimethylformamide suspension, and stirred at room temperature for 30 minutes at At the end of this time, 0.73 ml of bromoethionyl diethyl acetal was added to the mixture under ice cooling, and the mixture was stirred at 50 ° C for 3 hours. The dimethylformate was distilled off under reduced pressure. Ammonium amine. The residue was diluted with water and adjusted to P 加入 by adding 1 N aqueous hydrochloric acid solution, and then extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydroxide and dried over anhydrous sodium sulfate. The solvent was removed by autoclaving. The residue was purified by silica gel column chromatography using a mixture ratio of hexane and ethyl acetate as the eluent in a volume ratio of 2: 600 to obtain 60 mg of the title compound with R f = 0 · 4 6 (On silica thin layer chromatography, a 2: 1 mixture of hexane and ethyl acetate was used as the developing solvent.) Example 3 Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (please read the back Please fill in this page again) Argon acetone) Jie 1 favor _ pyridine-2,4-two _ will dissolve 20 ml of 6! &Lt; hydrochloric acid in water Add 10.07 g of 5- [4- (2,2-diethoxyethoxy) benzyl] -oxazolyl-2,4-dihexyl (prepared as in Example 2) in 80 ml of tetrahydrofuran, and Let it stand at room temperature overnight. At the end of this time, the solvent was distilled off under reduced pressure. The residue was diluted with water and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was passed through a silica gel column. Chromatographic purification, using a 2: 3 volume ratio of hexane and ethyl acetate as the eluent, 5.92 g of the title compound -157- This paper size applies to China National Standards (CNS) Α4 specifications (210X297 mm) ~ 503237

With Rf = 0.37 (on silica thin layer chromatography, using a 1: 2 volume ratio of hexane and ethyl acetate as the developing solvent). Example 4 5 ~ ί 4 ~ ί 2 ~ (1.3 ~~ Secondary pentamyl-2-yl) ethoxy group J Benzyl I thiazolidine-2,4-dione 'Repeat steps similar to those described in Example 2, In addition to using 15.0 grams of 5-(4-hydroxybenzyl) carbazolidine-2, 4-dihydrazone, 8.80 grams of sodium hydride (a 55% by weight dispersion in mineral oil), 17 ml of 2,-(2-bromoethyl) -1,3-dioxane and 80 ml of dimethylformamide, and the product was purified by silica gel column chromatography using a 1: 1 volume ratio A mixed solution of hexane and ethyl acetate was used as an eluent to obtain 6.67 g of the title compound, which was melted at 102-1 Q 4 ° C. Example 5 5- (4- (3-argon-propargonium) alkoxide 1-pyridine-2.4-di-_ 6.30 g 5- (4- [2- (1,3 -di-pentopent-2-yl ) Ethoxy] Benzyl} Blazolidine-2,4-Dihydrazine 1 (prepared as described in Example 4) 50 Printed by the Shellfish Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (Please read the notes on the back before filling (In this page) A mixture of 4: 1 acetic acid and water is stirred for 6 hours at 6 GT. At the end of this time, the solvent is distilled off under reduced pressure. The residue is purified by silica gel column chromatography using 1: 1 volume ratio of hexane and acetic acid. The ethyl acetate mixture was used as an eluent to obtain 2. 20 g of the title compound, which was melted at 48-51 ° C. Preparation Example 1 4-Phosphorus is very cool. Pyrosol is 56 g of 4-nitrophenol, 90 g. A solution of methyl bromoacetate and 500 g of dimethylformamide in 100 g of potassium sulfonate was stirred at room temperature for 2 days. At this time -15 8- This paper size applies to China National Standard (CNS) A4 (210X297) (Mm) 503237 A7 B7 V. Explanation of the invention () At the end of the period, dimethylformamide was distilled off under reduced pressure. The obtained residue was diluted with water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sulfuric acid. After decompression The solvent was removed. The residue was ground and crystallized with hexane to obtain 63.3 g of the title compound, which was melted at 9 8-9 9 ° C. Preparation Example 2 · 4-Aminophenoxyacetic acid methyl ester 30, δ 4 -Methyl phenylbenzene acetoacetate (prepared as described in Preparation Example 1), 10% w / w rake / sulfur of 5.0 g and 500 ml of methanol, 30 minutes at room temperature in a hydrogen atmosphere, 601C for 2 hours and 801C 3 After stirring for an hour, the catalyst was filtered off, concentrated under reduced pressure, and chromatographed on a silica gel column (hexane: ethyl acetate = 2: 1) to obtain 25. δ of the title compound having Rf di 0.79 (in a thin layer of silica gel) Chromatographically, ethyl acetate was used as the developing solvent. Preparation Example 3 4- (2-Bromo-2-butoxycarbonylethyl) phenoxyacetic acid methyl ester was cooled to 47% of 98 g under ice cooling. w / v Hydrobromic acid aqueous solution and 33 ml of an aqueous solution containing 12.8 g of sodium nitrite was added dropwise to 263 ml of 25.8 g of 4-aminobenzyl methyl acetate (prepared as described in Preparation Example 2) 2: 5 Volume ratio of methanol and acetone mixed solution, under ice cooling

It mixes for 3 Q minutes. Thereafter, 18.2 g of butyl acrylate was added. The mixture is printed at the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (please read the precautions on the back before filling this page); stir for 30 minutes under ice cooling and add 3.2 grams of copper bromide (I) and mix in the room. The mixture was stirred at room temperature overnight. At the end of this time, the solvent was distilled off under reduced pressure. The residue was diluted with aqueous sodium chloride solution and extracted with ethyl acetate. After the extract was washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to obtain 51.7 g of a crude product containing the title compound and having a counter-productivity [= 0.46 (in -159- this paper is applicable to Chinese countries) Standard (CNS) A4 specification (210X297 mm) _ 503237 A7 B7 V. Description of the invention () For thin layer silica gel chromatography, a 5: 1 volume ratio of hexane and ethyl acetate mixed solution is used as the developing solvent). Production Example 4 5-ί4- (1Η-Mipiyou, "4.5-bl pyridin-2-one methylargonyl 1 benzyl) oxazodine-2. 4-di (compound N 0. -9-9) will be 1.13 grams of 4- (ethoxycarbonylmethylamino) benzylcarbazolidine-2,4-diamine (as in Example 1 and Example 1) was added to 200 mg of 2,3-diaminopyridine, and Stir for 2 days at 110 ° C. At the end of this time, treat the reaction mixture with a 3 N aqueous hydrochloric acid solution and add ammonia to make it alkaline. The aqueous mixture is evaporated to dryness under reduced pressure, and The residue was purified by silica gel column chromatography, and a gradient elution method was used to obtain a 10 ·· 1 volume ratio of ethyl acetate and methanol as the eluent. The product was milled and crystallized with ethyl acetate to obtain 4 QQ mg. The title compound was melted at 2 4 7-2 4 8 ° C. Preparation Example 5 S- (4- (2-methyl-6-6-trimethylamine) "5.4-hl pyridine-2- 2-methylargine" Benzyl 1 favors _pyridine-2.4-di _ (&f; fh compound Hn.1-1: ^) Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs (please read the precautions on the back before filling this page) · 16 grams of 5- (4- (2-oxethoxy) benzyl) pyrazolid-2,4-two countries (as described in Example 3 Preparation) Add 3.00 g of 3-amino-2-methylamino-5-trifluoromethylpyridine to a solution of 6 ml of ethanol and 6 ml of acetic acid, and stir at room temperature for 4 hours. At the end of the time, the solvent was evaporated under reduced pressure. To the residue were added 50 ml of 1,2-dimethylaminoethane and 5.2 g of iodine, and the mixture was stirred at 60 ° C for one day. At the end of this time, the reaction mixture was poured into After the water, it was extracted with ethyl acetate. The extract was extracted with sodium ammonium water-16 0- This paper size is applicable to Chinese National Standard (CNS) A4 (210X297 mm) ~ 503237 A7 B7 V. Description of the invention () Solution cleaning and After drying with anhydrous sulfuric acid pin, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography, using a 1: 1 volume ratio of hexane and ethyl acetate as the eluent. The product was rolled and crystallized with ethyl acetate 52.0 mg of the title compound was melted at 2 1 2-2 1 4 ° C. Preparation Example 6. 5- (4- (3- (4-Gabenzyl)) _ # pyridin-2 -Yita Tianqi) benzyl) _ pyridine-2.4-two circles (Compound No. 1-1 34) Repeat the procedure similar to that described in Preparation Example 5 except that 1.2Q g of 3-amino- 2- (4- atmosphere Benzyl) aminopyridine (prepared as described in Preparation Example 3), 1.36 g of 5- [4- (2-Gasethylbenzyl) benzyl] Qazolidin-2,4-Difluorene 1 (as in Example 3 The preparation), 3 ml of ethanol, 3 ml of acetic acid, 1.69 g of iodine, and 25 ml of 1,2-dimethylaminoethane, the title compound was obtained as a crude product. This crude product was purified by silica gel column chromatography, and a gradient elution method was used, and a mixed solution of hexane and ethyl acetate in a volume ratio of 1: 1 to 1: 2 was used as an eluent to obtain (κ 4 〇 檫 of the title Compound, melted at 2 1 1-2 1 3 ° C. Preparation Example 7 Printed by the Consumer Cooperatives of the Central Standards Bureau, Ministry of Economic Affairs, Nitro-2-anilinopyridine (Please read the precautions on the back before filling this page). Order 15 g of 2-chloro-3-nitropyridine, 13, 22 g of aniline, and 25.07 g of sodium sulfonate in 180 ml of toluene. After stirring at room temperature for 8 hours, toluene was distilled off, water was added and ethyl acetate was added. Extraction, washing with brine, drying over sodium sulfate, and distilling off the solvent under reduced pressure. The obtained crude product was purified by silica-column chromatography using a 1: 5 volume ratio of ethyl acetate and hexane mixed solution to obtain 6, 9 Gram of the title compound, which melts at 66-68 ° C. -16 The paper size is applicable to Chinese National Standard (CNS) A4 (21〇2197 mm) ~ 503237 A7 B7 5. Description of the invention () 靱 Preparation Example 8 ^- mm -2- ^ mmm, repeating the steps described in Preparation Example 2, except: r 6.9 g of 3-nitro-2 -anilinopyridine (such as Prepared in Preparation Example 7) Hydrogenation was performed in the presence of 1.38 g of 10% w / w carbon / carbon in 150 ml of ethanol and 50 ml of the dilute compound solution. After the product was operated as described in Example 6, 4 was obtained. · 2 g of the title compound, which melted at 1 37-1 40 ° C. Preparation Example 9 5- (4- (3- 荣 某 眯 _ # 「5.441 卅 定 -2- 某甲 氲 某） Policy-Taka Azole-2, 4-di-! (Compound No. 0.1-161) Repeat the procedure similar to that described in Preparation Example 5 except that 2.78 g of 3-amino-2-anilinopyridine (as in Preparation Example (Prepared as described in 8), 3.98 grams of 5- [4- (2-gasethoxy) benzylpyrazolidine-2,4-dihydrazone (prepared as described in Example 3), 4.9 grams of iodine, 6 Ethanol, 6 ml of acetic acid and 50 ml of 1,2-dimethylaminoethane. After the product was operated as described in Preparation 5, the crude product obtained was purified by silica gel column chromatography using a volume of 1: 2. Compared with hexane and ethyl acetate mixed liquid as the eluent, 400 mg of the title compound can be obtained and melted at 88-91 ° C. Dance Preparation Example 10 Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs (please first (Read the notes on the back and fill out this page) The even-nitro 1-pyridine was repeated in a similar manner to that described in Preparation Example 7 except that 2 4 · 9 g of 2-ammonia-3-nitropyridine, 41.7 g of sodium sulfonate, and 22.7 ml of methylamine 3% ethanol The solution was reacted in 250 ml of toluene. After the product was operated as described in Preparation Example 7 «, the obtained crude product was ground and crystallized by isopropanol to obtain 2 4 · 0 g of the standard compound in 5 2-5 Dissolve at 3 ° C. -162- This paper size applies Chinese National Standard (CNS) A4 specification (210X297 mm) _ Printed by the Employees' Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs 503237 A7 B7 V. Description of the invention () Preparation example 11-Fang-2-_ Very amine and even apyridine were repeated in the same steps as in Preparation Example 2 except that 5. Q 0 g of 2-methylamino-3 -nitropyridine (prepared as described in Preparation Example 10) in 80 ml of I, 4 -Dipyridane, hydrogenated in the presence of 1.0 g of 10% w / w barium / carbon. After the product was worked up as described in Preparation Example 2, 3.87 g of the title compound was obtained, and was melted at 9 Q-9 2 ° C. Production Example 1 2 IS-f 4-Γ 2-(· 3 -methyazolazole Γ 5. 4-b 1 Fuyou -2-even), argon)) hydrazine-2.4-second brew 1 (Compound) Repeat steps similar to those described in Preparation Example 5, except that Q. 34 grams of 3-amino-2-methylaminopyridine (prepared as described in Preparation Example 11), 2. 10 grams of 5- [4 -(3-oxopropoxy) benzyl] ifazolidine-2,4-dihedron (prepared as described in Preparation 5), 6 ml of ethanol, 3 ml of acetic acid, 2.32 g of iodine and 30 ml Of 1,2-dimethoxy.ylethane. After the product was operated as described in Preparation Example 5, the obtained crude product was purified by silica gel column chromatography using ethyl acetate as an eluent. 85 g of the title compound were obtained and were melted at 96-100 ° C. Preparation Example 1 3 3-amino-2- (4-chlorobenzyl) aminopyridine was mixed with 5.00 g of 2- (4-chlorobenzyl) amino-3-nitropyridine (prepared as described in Preparation Example 14). ), 21.4 g of tin (II) dichloride dihydrate, and 150 ml of 9: 1 volume ratio of ethyl acetate and 2-methyl-2-propanol, stirred at 60¾ for 1 hour and then added 0 · 36 Gram of sodium borohydride and stirring at 60P 3 -163-This paper size applies the Chinese National Standard (CNS) A4 specification (210 ^ 297 mm) (Please read the precautions on the back before filling this page) Order 503237 A7 B7 5 2. Description of the invention After () hours, the solvent was distilled off under reduced pressure. The obtained residue was diluted with water and neutralized by adding a potassium sulfonate aqueous solution, and then extracted with ethyl acetate. After the extract was washed with an aqueous sodium chloride solution and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The obtained residue was ground and crystallized by using a mixed solution of ethyl acetate and hexane to obtain 3.55 g of a standard compound, which was melted at 1 2-1 2 5 ° C. Preparation Example 1 4 -U-Gabenzylamine) Pyridine A mixture of 10.3 g of 2-hydroxy-3-nitropyridine and 25.5 ml of thionyl chloride was put under a stream of water. After 2.5 hours of heating, 1.1 ml of dimethylformamide was quickly added, and then heated for 2.5 hours under sulfur return. At the end of this time, the solvent was evaporated under reduced pressure. To the obtained residue were added 80 ml of toluene and 19.1 g of sodium geranate, and then 12.3 ml of 2-Q benzylamine in 2 Q ml of a toluene solution was added dropwise, followed by stirring at 8 5 ° C for 4 hours. At the end of this time, insoluble matter was filtered off. The filtrate was washed with water and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was crystallized by milling with 2-propanol to obtain 12.0 g of the title compound, which was melted at 95-96 ° C. Please read the note at the back of the page first printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs -164 This paper size applies to the Chinese National Standard (CNS) Α4 specification (210X297 mm)

Claims (1)

503237 503237 6. Apply for a patent scope 5. If the compound of the patent scope item 1 is applied, it 6. If the patent scope of the application item 1 is applied, it 7. If the patent scope of the application item 1 is applied, it 8. If the patent is applied for The compound of the scope item 1, its sulfur. 9. If the compound in the scope of patent application No. 8 is applied, its compound group, 1.4 compound oxygen or halogen atom. 10. As for the compound in the scope of patent application item 8, its methoxy, ethoxy, fluorine atom or chlorine atom. 11. As for the compound in the scope of patent application No. 8, its methoxy group. 12 The compound as claimed in claim 8 wherein R is a hydrogen atom. Where Y is an oxygen atom. Where Y 'is a sulfur atom. Where Y is oxygen, Y 'is where R is a hydrogen atom, where R is a hydrogen atom, where R is a hydrogen atom, and where R is a hydrogen atom.